original_index int64 2 1.77M | extracted_from_file stringclasses 489
values | date_of_experiment timestamp[ns]date | grant_date timestamp[ns]date 1976-01-01 00:01:00 2016-01-01 00:09:00 | is_mapped bool 1
class | rxn_str stringlengths 87 6.12k | reactant_000 stringlengths 1 902 | reactant_001 stringlengths 1 902 ⌀ | reactant_002 null | agent_000 stringlengths 1 540 ⌀ | agent_001 stringlengths 1 852 ⌀ | agent_002 stringlengths 1 247 ⌀ | agent_003 null | agent_004 null | agent_005 null | agent_006 null | agent_007 null | agent_008 null | agent_009 null | agent_010 null | agent_011 null | agent_012 null | agent_013 null | agent_014 null | agent_015 null | agent_016 null | solvent_000 stringclasses 446
values | solvent_001 stringclasses 405
values | solvent_002 null | solvent_003 null | solvent_004 null | solvent_005 null | solvent_006 null | solvent_007 null | solvent_008 null | solvent_009 null | solvent_010 null | temperature float64 -230 30.1k ⌀ | rxn_time float64 0 2.16k ⌀ | procedure_details stringlengths 8 24.5k | product_000 stringlengths 1 484 | product_001 null | yield_000 float64 0 90,205,156,600B ⌀ | yield_001 float64 0 100M ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1,268,641 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]([F:15])([F:14])[F:13])[C:3]=1[C:4](O)=[O:5].CO>C1COCC1>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]([F:14])([F:13])[F:15])[C:3]=1[CH2:4][OH:5] | O=C(O)c1c(Br)cccc1OC(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CO | null | null | null | null | null | null | null | null | null | null | null | To a stirred solution of 2-bromo-6-[(trifluoromethyl)oxy]benzoic acid (1.116 g, 3.92 mmol, Parkway Scientific), in THF (45 ml), under nitrogen, was added 1.0 M borane-tetrahydrofuran complex (12 ml, 12 mmol) carefully over about 2 minutes. The solution was then heated at gentle reflux for 24 h and allowed to cool. Meth... | OCc1c(Br)cccc1OC(F)(F)F | null | 100.7 | null |
66,059 | ord_dataset-8af141577c90485cb9c91079a5ef96b3 | null | 1980-01-01T00:05:00 | true | N1C=CN=C1.[C:6]([C:8]1([OH:14])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)#[CH:7].CN(C)C=O.[CH3:20][Si:21]([CH3:24])([CH3:23])Cl>CCCCCC>[C:6]([C:8]1([O:14][Si:21]([CH3:24])([CH3:23])[CH3:20])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)#[CH:7] | C[Si](C)(C)Cl | C#CC1(O)CCCCC1 | null | c1c[nH]cn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCCCCC | null | null | null | null | null | null | null | null | null | null | 0.02 | A 194 g portion of imidazole and 158.2 g of 1-ethynylcyclohexan-1-ol are mixed with 500 g of dimethylformamide with cooling in an ice bath. A 152 g portion of trimethylchlorosilane is added with cooling and stirring in about one minute. The mixture is stirred for one hour and allowed to stand overnight. One liter of he... | C#CC1(O[Si](C)(C)C)CCCCC1 | null | null | null |
1,195,051 | ord_dataset-4e81c470cc3b429faf5e1caa50f70a98 | null | 2012-01-01T00:08:00 | true | Br[C:2]1[C:3]2[N:4]([C:8]([CH3:11])=[N:9][N:10]=2)[CH:5]=[CH:6][CH:7]=1.C([Sn](CCCC)(CCCC)[C:17](=[CH2:28])[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])CCC>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC... | Cc1nnc2c(Br)cccn12 | C=C(C(=O)OCc1ccccc1)[Sn](CCCC)(CCCC)CCCC | null | Cl[Cu] | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 60 | null | To a solution of 0.13 g (0.61 mmol) of 8-bromo-3-methyl[1,2,4]triazolo[4,3-a]pyridine from Step B above in 4 mL of anhydrous THF was added a solution of 0.36 g (0.80 mmol) of benzyl 2-(tributylstannyl)acrylate (see Intermediate 62, Step B) in 1 mL of anhydrous THF, 0.11 g (0.09 mmol) of tetrakis(triphenylphosphine)pall... | C=C(C(=O)OCc1ccccc1)c1cccn2c(C)nnc12 | null | 72.7 | null |
1,725,704 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | [CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:33])=[C:10]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)[C:11]=2[O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[C:6](=[O:34])[C:5]([C:35](O)=[O:36])=[CH:4]1)[CH3:2].ClC(OCC(C)C)=O.CC(C[AlH]CC(C)C)C>O1CCCC1.C1(C)C=CC=... | CCn1cc(C(=O)O)c(=O)c2cc(F)c(OCc3ccc(OC)cc3)c(OCc3ccc(OC)cc3)c21 | null | null | CC(C)COC(=O)Cl | CC(C)C[AlH]CC(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 1 | To a suspension of 1-ethyl-6-fluoro-7,8-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (40 g, 79 mmol) in Tetrahydrofuran (THF) (300 mL) was added TEA (12.08 mL, 87 mmol) and isobutyl chloroformate (11.39 mL, 87 mmol). The resulting mixture was stirred at r.t. for 1 h. LCMS showed completion of ... | CCn1cc(CO)c(=O)c2cc(F)c(OCc3ccc(OC)cc3)c(OCc3ccc(OC)cc3)c21 | null | 65.2 | null |
565,664 | ord_dataset-5c8a417a8ba04cf0b7f78b9db9af1d01 | null | 2002-01-01T00:10:00 | true | Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[N+:12]([C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1)([O-:14])=[O:13].C(=O)([O-])[O-].[K+].[K+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC... | O=[N+]([O-])c1cccc(B(O)O)c1 | O=C1Cc2cc(Br)ccc2N1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCOC | O | null | null | null | null | null | null | null | null | null | 25 | 0.25 | 5-bromo-2-indolinone (1.08 g, 5.09 mmol) and tetrakistriphenyl phosphine Pd (0) (0.273 g) were stirred under an atmosphere of nitrogen in ethylene glycol dimethyl ether (35 mL). After 15 minutes, 3-nitrophenyl boronic acid (1.70 g, 10.2 mmol) was added, followed by potassium carbonate (4.24 g, 30.7 mmol) in water (15 m... | O=C1Cc2cc(-c3cccc([N+](=O)[O-])c3)ccc2N1 | null | 6.5 | null |
1,400,758 | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | null | 2014-01-01T00:02:00 | true | Cl.[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][NH2:10])=[N:7][CH:8]=1.[CH:11](O)=[O:12].[OH-].[NH4+]>O>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][NH:10][CH:11]=[O:12])=[N:7][CH:8]=1 | NCc1ccc(Cl)cn1 | O=CO | null | Cl | [NH4+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 0 | null | A solution of (5-chloropyridin-2-yl)methanamine hydrochloride (1.0 g, 5.31 mmol) in formic acid (5.09 g, 4.24 mL, 106 mmol) was refluxed at 110° C. After 20 h the reaction was cooled to 0° C. and 25% ammonium hydroxide in water was added until pH˜9 was reached. The mixture was diluted with water and then extracted into... | O=CNCc1ccc(Cl)cn1 | null | null | null |
1,657,910 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [F:1][C:2]1([F:34])[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[C@@H:4]([C:19]([NH:21][C@H:22]([C:24]2[CH:33]=[CH:32][C:27]([C:28]([O:30]C)=[O:29])=[CH:26][CH:25]=2)[CH3:23])=[O:20])[CH2:3]1.O[Li].O>>[F:34][C:2]1([F:1])[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[C... | COC(=O)c1ccc([C@H](C)NC(=O)[C@H]2CC(F)(F)CCN2Cc2ccc(C(F)(F)F)cc2)cc1 | null | null | [Li]O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | null | null | The title compound (E16) (15 mg) was prepared according to the general procedure for esters hydrolysis (Method D) starting from methyl 4-((S)-1-((R)-4,4-difluoro-1-(4-(trifluoromethyl)benzyl)piperidine-2-carboxamido)ethyl)benzoate (D135) (20 mg). (LiOH H2O: 4 eq; reaction time: 18 hrs) | C[C@H](NC(=O)[C@H]1CC(F)(F)CCN1Cc1ccc(C(F)(F)F)cc1)c1ccc(C(=O)O)cc1 | null | 77.2 | null |
266,833 | ord_dataset-a2ae447c4340438c8c3a827109aeb425 | null | 1993-01-01T00:04:00 | true | C(=O)([O-])[O-].[K+].[K+].O.[NH2:8][CH:9]1[CH2:18][CH2:17][C:16]2[CH:15]=[C:14]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:13]=[CH:12][C:11]=2[CH2:10]1.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>C(OCC)(=O)C>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([NH:8][CH:9]2[CH2:18][CH2... | O=S(=O)(Cl)c1ccc(Cl)cc1 | CCOC(=O)Cc1ccc2c(c1)CCC(N)C2 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 25 | null | 2.99 g of potassium carbonate, 20 ml of ethyl acetate and 40 ml of water are added to 2.09 g of ethyl (+)-6-amino-5,6,7,8-tetrahydronaphthalene-2-acetate 1/2 (+)-D-dibenzoyltartrate, and a solution of 1.28 g of 4 -chlorophenylsulfonyl chloride in 20 ml of ethyl acetate is added thereto at room temperature under stirrin... | CCOC(=O)Cc1ccc2c(c1)CCC(NS(=O)(=O)c1ccc(Cl)cc1)C2 | null | 84.9 | null |
736,385 | ord_dataset-76dd1b78ee414d2da0ed30700ef026f7 | null | 2006-01-01T00:10:00 | true | [C:1]1([C:7]2[CH:12]=[CH:11][N:10]3[C:13]([CH:16]=[O:17])=[CH:14][N:15]=[C:9]3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S([CH2:28][N+:29]#[C-:30])(C1C=CC(C)=CC=1)(=O)=O.C([O-])([O-])=O.[K+].[K+]>CO>[O:17]1[C:16]([C:13]2[N:10]3[CH:11]=[CH:12][C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[CH:8][C:9]3=[N:15][CH:14]=2)... | O=Cc1cnc2cc(-c3ccccc3)ccn12 | [C-]#[N+]CS(=O)(=O)c1ccc(C)cc1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | 7-Phenylimidazo[1,2-a]pyridine-3-carbaldehyde (7-1, 0.030 g, 0.14 mmol), tosylmethyl isocyanide (0.032 g, 0.16 mmol) and K2CO3 (0.022 g, 0.16 mmol) were dissolved in 1 ml MeOH and the resulting solution was heated to reflux. After 4 h the reaction was quenched by the addition of water. The resulting mixture was extract... | c1ccc(-c2ccn3c(-c4cnco4)cnc3c2)cc1 | null | null | null |
686,681 | ord_dataset-56747de2718a4ac5bf061651d1cc9e3e | null | 2005-01-01T00:10:00 | true | Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[CH:12][S:11][C:10]=2[CH:21]=1.[NH:22]([CH2:26][CH2:27][OH:28])[CH2:23][CH2:24][OH:25]>>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]2[C:9]3[CH:8]=[CH:7][C:6]([O:5][CH2:4][CH2:3][CH2:2][N:22]([CH2:26][CH2:27][... | Fc1ccc(-c2csc3cc(OCCCBr)ccc23)cc1 | OCCNCCO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In analogy to example 3.1, 6-(3-Bromo-propoxy)-3-(4-fluoro-phenyl)-benzo[b]thiophene and diethanolamine were converted to yield 2-[{3-[3-(4-Fluoro-phenyl)-benzo[b]thiophen-6-yloxy]-propyl}-(2-hydroxy-ethyl)-amino]-ethanol as colorless oil, MS: 390 (MH+). | OCCN(CCO)CCCOc1ccc2c(-c3ccc(F)cc3)csc2c1 | null | null | null |
131,640 | ord_dataset-232d09663ed349c2a1fb1f05d411eae0 | null | 1985-01-01T00:07:00 | true | [CH3:1][O:2][C:3]1[C:11]([CH3:12])=[C:10]([CH3:13])[C:9]([O:14][CH3:15])=[C:8]([CH3:16])[C:4]=1[C:5]([OH:7])=O.[NH2:17][C:18]1[CH:19]=[C:20]([CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH:21]=[CH:22][C:23]=1[OH:24]>>[OH:24][C:23]1[CH:22]=[CH:21][C:20]([CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:19][C:18]=1[NH:17][C:5](=[O:7]... | COC(=O)Cc1ccc(O)c(N)c1 | COc1c(C)c(C)c(OC)c(C(=O)O)c1C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 2,5-Dimethoxy-3,4,6-trimethylbenzoic acid (m.p. 98°-100° C. was reacted with methyl 3-amino-4-hydroxyphenylacetate to give methyl 4-hydroxy-3-(2,5-dimethoxy-3,4,6-trimethylbenzoylamino)phenylacetate [m.p. 159°-160° C., δ 2.14 (3H), 2.20 (3H), 2.32 (3H), 3.48 (2H), 3.65 (6H), 3.70 (3H), 7.02 (3H), 8.30 (1H), 8.87 (1H)] ... | COC(=O)Cc1ccc(O)c(NC(=O)c2c(C)c(OC)c(C)c(C)c2OC)c1 | null | null | null |
576,484 | ord_dataset-f4512fe8cd804ac79da66cbc0c2b9d42 | null | 2002-01-01T00:12:00 | true | C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:19])[CH:8]=[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:10]2)=[CH:5][CH:4]=1.B(Br)(Br)Br.CO>C(Cl)Cl>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:19])[CH:8]=[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:10]2)=[CH:5][CH:4]=1 | COc1ccc2c(=O)cc(-c3ccccc3)oc2c1 | null | null | BrB(Br)Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | ClCCl | null | null | null | null | null | null | null | null | null | null | 1 | 100 mg (0.4 mmol) of compound 7-methoxy-2-phenyl-chromen-4-one obtained in Example 2 was dissolved in methylenechloride, and 2.0 molar equivalents of BBr3 was added thereto. The mixture was stirred for 1 hour. Methanol was added to the mixture, and then solvent was removed by distillation under reduced pressure. The re... | O=c1cc(-c2ccccc2)oc2cc(O)ccc12 | null | 64 | null |
1,439,862 | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | null | 2014-01-01T00:06:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[C:4]([O:11][C@@H:12]2[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]2[OH:18])[CH:3]=1.[H][H]>CO.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([O:11][C@@H:12]2[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]2[OH:18])[CH:3]=1 | [H][H] | O=[N+]([O-])c1ccc(F)cc1O[C@@H]1CCCC[C@H]1O | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | (R,R)-4-Fluoro-2-(2-hydroxycyclohexyloxy)-nitrobenzene (1.99 g) in methanol (20.0 ml) was hydrogenated under 50 psi hydrogen for 5 h at rt using palladium on charcoal (5%) (200 mg) as catalyst. The catalyst was filtered off; the resulting solution was evaporated to dryness to yield an oil. | Nc1ccc(F)cc1O[C@@H]1CCCC[C@H]1O | null | null | null |
497,412 | ord_dataset-9df8b3ec9c8742b3802e0efaac6f6ef3 | null | 2001-01-01T00:03:00 | true | [H-].[Na+].[NH:3]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])[C:6]=2[CH:5]=[CH:4]1.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>O1CCCC1>[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28]([N:3]2[C:11]3[CH:10]=[CH:9][CH:8... | O=C(OCc1ccccc1)c1cccc2[nH]ccc12 | Cc1ccc(S(=O)(=O)Cl)cc1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 0 | 1 | To a suspension of sodium hydride (133 mg) in tetrahydrofuran (5.0 ml) was added dropwise a solution of benzyl indole-4-carboxylate (580 mg) in tetrahydrofuran (5.0 ml) at 0° C. and the mixture was stirred at 0° C. for 1 hour. 4-Toluenesulfonyl chloride (440 mg) was added to the mixture and the solution was stirred at ... | Cc1ccc(S(=O)(=O)n2ccc3c(C(=O)OCc4ccccc4)cccc32)cc1 | null | 59.8 | null |
427,224 | ord_dataset-8cce6f317d644b348a7978a2dce3ea01 | null | 1999-01-01T00:03:00 | true | [N:1]1([C:6]2[CH:17]=[CH:16][C:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][NH2:15])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.N1C=CC=CC=1.[CH3:24][O:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1>ClCCl>[CH3:24][O:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([NH:15][CH2:14][CH2:13][CH2:12][CH2:11][O:10][C:9... | NCCCCOc1ccc(-n2ccnc2)cc1 | COc1ccc(C(=O)Cl)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | c1ccncc1 | null | null | null | null | null | null | null | null | null | -10 | 18 | A solution of 2.3 g of 4-[4-(1H-imidazol-1-yl)phenoxy]butaneamine (Example 2) in 50 ml of dichloromethane containing 2 ml of pyridine is treated with 2.0 g of 4-methoxybenzoyl chloride. The reaction mixture is allowed to stand at room temperature for 18 hours, and is then heated at reflux for one hour. The volatiles ar... | COc1ccc(C(=O)NCCCCOc2ccc(-n3ccnc3)cc2)cc1 | null | null | null |
1,394,772 | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | null | 2014-01-01T00:02:00 | true | [CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][C:11]=2[CH3:19])=[CH:5][C:4]=1[N+:20]([O-])=O.[H][H]>C(OCC)(=O)C.C(O)C.[Pd]>[NH2:16][C:13]1[CH:14]=[CH:15][C:10]([O:9][C:6]2[CH:5]=[C:4]([NH2:20])[C:3]([NH:2][CH3:1])=[CH:8][CH:7]=2)=[C:11]([CH3:19])[CH:12]=1 | [H][H] | CNc1ccc(Oc2ccc([N+](=O)[O-])cc2C)cc1[N+](=O)[O-] | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | To a solution of N-methyl-4-(2-methyl-4-nitrophenoxy)-2-nitrobenzenamine (1.90 g, 6.27 mmol) in ethyl acetate (10 mL) and ethanol (20 mL) was added 10% Pd/C (0.342 g, 0.321 mmol). After shaking under 50 psi of hydrogen for 1 hour, the mixture was filtered and the filtrate was concentrated under reduced pressure to prov... | CNc1ccc(Oc2ccc(N)cc2C)cc1N | null | null | null |
1,509,023 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | C([O:5][C:6](=O)[NH:7][CH2:8][CH2:9][CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH:20]=[O:21])=[CH:12]1)(C)(C)C.Cl.[CH2:24](N(CC)CC)C.C(Cl)(=O)C>ClCCl>[CH:20]([C:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:11]([CH2:10][CH2:9][CH2:8][NH:7][C:6](=[O:5])[CH3:24])[CH:12]=1)=[O:21] | CC(C)(C)OC(=O)NCCCn1cc(C=O)c2ccccc21 | CCN(CC)CC | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)Cl | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 1 | To a stirred dichloromethane (0.09 M) solution of tert-butyl[3-(3-formyl-1H-indol-1-yl)propyl]carbamate from the previous step was added HCl (4 N solution in dioxane, 45 eq.). The resulting solution was stirred at RT for 1 h before the volatiles were removed in vacuo. Dichloromethane was then added to the red residue a... | CC(=O)NCCCn1cc(C=O)c2ccccc21 | null | null | null |
517,731 | ord_dataset-a495451286334c5c9bbcbd48a00c1350 | null | 2001-01-01T00:09:00 | true | [CH2:1]([O:8][C:9]([NH:11][CH:12]1[N:18]=[C:17]([CH2:19][CH3:20])[C:16]2[CH:21]=[CH:22][CH:23]=[C:24]([CH3:25])[C:15]=2[N:14]([CH2:26][C:27]([O:29]CC)=[O:28])[C:13]1=[O:32])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>COCCOC.C(OCC)(=O)C.Cl>[CH2:1]([O:8][C:9]([NH:11][CH:12]1[N:18]=[C:17]([CH2:19][CH3:20]... | CCOC(=O)CN1C(=O)C(NC(=O)OCc2ccccc2)N=C(CC)c2cccc(C)c21 | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | COCCOC | null | null | null | null | null | null | null | null | null | 25 | 8 | A mixture of (3RS)-3-benzyloxycarbonylamino-2,3-dihydro-5-ethyl-1-ethoxycarbonylmethyl-9-methyl-1H-1,4-benzodiazepin-2-one (1.55 g) and 1N sodium hydroxide (7.0 ml) in 1,2-dimethoxyethane (10 ml) was stirred at room temperature overnight. The reaction mixture was evaporated in vacuo to afford a residue, which was disso... | CCC1=NC(NC(=O)OCc2ccccc2)C(=O)N(CC(=O)O)c2c(C)cccc21 | null | 84.1 | null |
208,225 | ord_dataset-ac1c7aa04d6c4e588e723e3e05721681 | null | 1990-01-01T00:05:00 | true | C(OC(N1CCC[C@H]1/C=C(/[C:15]1[CH2:21][C@H:20]2N([C:18](=O)[C@@H:19]2[C@H:22]([OH:24])C)[C:16]=1[C:26](OCC=C)=O)\C)=O)C=C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC1(C)CC(=[O:58])CC(=O)C1>O1CCCC1.C(O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=... | CC1(C)CC(=O)CC(=O)C1 | C=CCOC(=O)C1=C(/C(C)=C/[C@@H]2CCCN2C(=O)OCC=C)C[C@@H]2[C@@H]([C@@H](C)O)C(=O)N12 | null | [Pd] | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCO | null | null | null | null | null | null | null | null | null | 25 | 1 | To a solution of allyl (5R,6S)-3-[(E)-2-{(2S)-1-allyloxycarbonylpyrrolidin-2-yl}-1-methylethenyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (2.82 g) in a mixture of tetrahydrofuran (28 ml) and ethanol (14 ml) were added successively triphenylphosphine (0.51 g), 5,5-dimethyl-1,3cyclohexan... | CCCCC=C(C)C(=O)O | null | 163.2 | null |
105,022 | ord_dataset-4ac1b977dc504cb5a6a8e85d7d777c45 | null | 1983-01-01T00:05:00 | true | [CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][C@@H:9]([OH:12])[C@H:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7]1)=[O:5])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:38][C:39]1[CH:40]=[C:41](O)[CH:42]=[CH:43][CH:44]=1.N(C(OCC)=O)=NC(OCC)=O>C1C=CC=CC=1.CCOCC>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][C@H:9](... | CCOC(=O)N1CC[C@@H](O)[C@H](c2ccccc2)C1 | Oc1cccc(F)c1 | null | CCOC(=O)N=NC(=O)OCC | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccccc1 | CCOCC | null | null | null | null | null | null | null | null | null | 25 | 8 | To a mixture of 6.23 g of trans-1-ethoxycarbonyl-3-phenyl-4-piperidinol, 7.21 g of triphenylphosphine and 2.49 ml of m-fluorophenol in 250 ml of anhydrous benzene is added dropwise under nitrogen at 5° C. over a 90 minute period a solution of 4.79 g of diethyl azodicarboxylate in 250 ml of benzene. After the addition i... | CCOC(=O)N1CC[C@H](Oc2cccc(F)c2)[C@H](c2ccccc2)C1 | null | null | null |
1,295,278 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | C([O:4][CH2:5][CH2:6][N:7]1[C:15]([C:16]([OH:19])([CH3:18])[CH3:17])=[N:14][C:13]2[C:8]1=[N:9][C:10](Cl)=[N:11][C:12]=2[N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)(=O)C.[CH3:27][C:28]1[C:33](B2OC(C)(C)C(C)(C)O2)=[CH:32][N:31]=[C:30]([NH2:43])[N:29]=1>>[NH2:43][C:30]1[N:29]=[C:28]([CH3:27])[C:33]([C:10]2[N:9]=[C:8]3[... | CC(=O)OCCn1c(C(C)(C)O)nc2c(N3CCOCC3)nc(Cl)nc21 | Cc1nc(N)ncc1B1OC(C)(C)C(C)(C)O1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 2-(2-Chloro-8-(2-hydroxypropan-2-yl)-6-morpholino-9H-purin-9-yl)ethyl acetate (300 mg) was treated with 4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine via General Procedure A and was purified via reverse phase HPLC to give 107 mg of 102 as a white solid. MS (Q1) 415.2 (M)+ | Cc1nc(N)ncc1-c1nc(N2CCOCC2)c2nc(C(C)(C)O)n(CCO)c2n1 | null | null | null |
1,006,042 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | [Br-:1].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.[CH:34]([C:37]([C:39]1[CH:52]=[CH:51][C:42]2[O:43][C:44]([F:50])([F:49])[C:45]([F:48])([F:47])[O:46][C:41]=2[CH:40]=1)=[O:38])([CH3:36])[CH3:35]>O1CCCC1>[F:50][C:44]1([F:49])[O:43][C:42]2[CH:51]=[CH:52][C:39]([C:37]([C:34]([B... | [Br-] | CC(C)C(=O)c1ccc2c(c1)OC(F)(F)C(F)(F)O2 | null | C[N+](C)(C)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | 1.89 g of phenyltrimethylammonium tribromide was added to a mixture comprising 1.40 g of 2,2,3,3-tetrafluoro-1,4-benzodioxan-6-yl isopropyl ketone and 19.7 ml of tetrahydrofuran, followed by a reaction for two hours at room temperature. The reaction mixture was filtered, and the filtrate was concentrated under reduced ... | CC(C)(Br)C(=O)c1ccc2c(c1)OC(F)(F)C(F)(F)O2 | null | 171 | null |
1,043,696 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | [CH2:1]([C:4]1[S:13][C:7]2[N:8]=[CH:9][N:10]=[C:11](O)[C:6]=2[CH:5]=1)[CH2:2][CH3:3].O=P(Cl)(Cl)[Cl:16]>>[Cl:16][C:11]1[C:6]2[CH:5]=[C:4]([CH2:1][CH2:2][CH3:3])[S:13][C:7]=2[N:8]=[CH:9][N:10]=1 | CCCc1cc2c(O)ncnc2s1 | O=P(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 16 | The product of Example 3b was reacted with excess POCl3 at reflux for 3 h then at room temperature for 16 h. The reaction was poured over ice and partitioned between water and ethyl acetate. The organic layer was concentrated to provide the title compound. | CCCc1cc2c(Cl)ncnc2s1 | null | null | null |
1,511,259 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | [Si]([O:8][CH2:9][CH2:10][C@H:11]([NH:18][C:19]1[O:20][C:21]([CH3:35])([CH3:34])[CH:22]([C:27]2[CH:28]=[C:29]([CH3:33])[CH:30]=[CH:31][CH:32]=2)[S:23](=[O:26])(=[O:25])[N:24]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(C(C)(C)C)(C)C.Cl>CO.C(OCC)(=O)C>[CH3:34][C:21]1([CH3:35])[O:20][C:19]([NH:18][C@H:11]([C:12]2[C... | Cc1cccc(C2C(C)(C)OC(N[C@@H](CCO[Si](C)(C)C(C)(C)C)c3ccccc3)=NS2(=O)=O)c1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 25 | 16 | 51.7 mg of [(S)-3-(tert-butyldimethylsilanyloxy)-1-phenylpropyl]-(6,6-dimethyl-4,4-dioxo-5-m-tolyl-5,6-dihydro-4H-4lambda6-1,4,3-oxathiazin-2-yl)amine were dissolved in 2 ml of methanol, 0.1 ml of concentrated hydrochloric acid was added and the mixture was stirred at room temperature for 16 hours. The reaction solutio... | Cc1cccc(C2C(C)(C)OC(N[C@@H](CCO)c3ccccc3)=NS2(=O)=O)c1 | null | 56.9 | null |
1,257,009 | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | null | 2013-01-01T00:02:00 | true | [CH2:1]([O:8][C:9]1[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][C:10]=1[O:22][CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.S(Cl)([Cl:33])=O>CN(C)C=O>[CH2:1]([O:8][C:9]1[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][C:12]([C:13]([Cl:33])=[O:14])=[CH:11][C:10]=1[O:22][CH3:... | O=S(Cl)Cl | COc1cc(C(=O)O)cc(C(F)(F)F)c1OCc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | CN(C)C=O | null | null | null | null | null | null | null | null | null | 60 | 16 | To 4-benzyloxy-3-methoxy-5-trifluoromethylbenzoic acid (601 mg), toluene (6 mL), N,N-dimethylformamide (1 droplet) and thionyl chloride (0.16 mL) were added, and then the mixture was stirred at 60° C. for 16 hours. The solvent was distilled off under reduced pressure and then azeotroped with toluene to obtain the title... | COc1cc(C(=O)Cl)cc(C(F)(F)F)c1OCc1ccccc1 | null | null | null |
464,587 | ord_dataset-6c36eb0f817d4144988b8963c5d58879 | null | 2000-01-01T00:05:00 | true | C([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:31])[C:16]([O:26][CH2:27][CH2:28][CH2:29][CH3:30])([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:17]([CH3:19])[CH3:18])[CH2:10][CH2:9]1)C1C=CC=CC=1>C(O)C.[OH-].[Pd+2].[OH-].[C]>[NH:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15](=[O:31])[C:16]([O:26][CH2:27][CH2:28][CH2:29... | CCCCOC(C(=O)NC1CCN(Cc2ccccc2)CC1)(c1ccccc1)C(C)C | null | null | [Pd+2] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | 6 | To a solution of N-(1-benzyl-4-piperidinyl)-2-butoxy-3-methyl-2-phenylbutanamide (invention compound, Compound No. 4) (4.5 g, 10.6 mmole) in ethanol (60 ml) was added palladium hydroxide-carbon (1.2 g), followed by hydrogenation for 6 hours at room temperature. The catalyst was filtered off and the filtrate was removed... | CCCCOC(C(=O)NC1CCNCC1)(c1ccccc1)C(C)C | null | null | null |
868,962 | ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | null | 2009-01-01T00:03:00 | true | [CH2:1]([S:3]([CH2:6][CH2:7][C:8]12[CH2:15][CH2:14][C:11]([C:16]([NH:18][CH3:19])=O)([CH2:12][CH2:13]1)[CH2:10][CH2:9]2)(=[O:5])=[O:4])[CH3:2].C(Cl)(=O)C(Cl)=O.[F:26][C:27]([F:40])([F:39])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]1NN=[N:36][N:35]=1>C(Cl)Cl.CN(C=O)C>[CH2:1]([S:3]([CH2:6][CH2:7][C:8]12[CH2:15][C... | FC(F)(F)c1ccccc1-c1nnn[nH]1 | CCS(=O)(=O)CCC12CCC(C(=O)NC)(CC1)CC2 | null | O=C(Cl)C(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 1 | Methyl amide 10-5 (220 mg, 0.77 mmol) was dissolved in anhydrous methylene chloride (2 mL) and treated with oxalyl chloride (2M in methylene chloride, 0.77 mL, 1.54 mmol) and DMF (2 drops). The solution was stirred at room temperature for 1 h, then solvent removed by evaporation under diminished pressure. The residue w... | CCS(=O)(=O)CCC12CCC(c3nnc(-c4ccccc4C(F)(F)F)n3C)(CC1)CC2 | null | null | null |
302,546 | ord_dataset-bfcf5a01f1a04ec585ba3f28cb93c8c9 | null | 1995-01-01T00:01:00 | true | C(O[C:6]([NH:8][C@@H:9]([CH2:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[C@@H:10]([OH:18])[CH2:11][C@@H:12]([CH3:17])[C:13]([NH:15][CH3:16])=[O:14])=[O:7])(C)(C)C.Cl.[C:27]([O:31][C:32]([NH:34][C@H:35](C(O)=O)[CH2:36][C:37]1[N:38]=[CH:39][S:40][CH:41]=1)=[O:33])([CH3:30])([CH3:29])[CH3:28].C(P(=O)(OCC)OCC)#N.... | CNC(=O)[C@H](C)C[C@H](O)[C@H](CC1CCCCC1)NC(=O)OC(C)(C)C | CC(C)(C)OC(=O)N[C@@H](Cc1cscn1)C(=O)O | null | CCOP(=O)(C#N)OCC | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | C1COCCO1 | null | null | null | null | null | null | null | null | null | 25 | 0.5 | A mixture of 200 mg (0.56 mmole) of (2R, 4S, 5S)-5-(t-butoxycarbonyl)amino-6-cyclohexyl-4-hydroxy-2,N-dimethylhexanamide (prepared as described in Preparation 5) and 4 ml of a 4N solution of hydrogen chloride in dioxane was stirred at room temperature for 30 minutes. At the end of this time, the solvent was removed by ... | CNC(=O)[C@H](C)C[C@H](O)[C@H](CC1CCCCC1)NC(=O)[C@H](Cc1cscn1)NC(=O)OC(C)(C)C | null | 90.9 | null |
1,537,460 | ord_dataset-8d5c200bca27407ab9febe7598e16458 | null | 2015-01-01T00:01:00 | true | [P:1]([O:50]CC[Si](C)(C)C)([O:43]CC[Si](C)(C)C)([O:3][C:4]([CH3:42])([CH2:6][CH2:7][S:8]([N:11]1[CH2:16][CH2:15][C:14]([C:17]2[CH:41]=[CH:40][C:20]3[N:21]=[C:22]([O:24][CH:25]4[CH2:30][CH2:29][N:28]([C:31]5[N:36]=[CH:35][C:34]([CH2:37][CH2:38][CH3:39])=[CH:33][N:32]=5)[CH2:27][CH2:26]4)[S:23][C:19]=3[CH:18]=2)=[CH:13][... | CCCc1cnc(N2CCC(Oc3nc4ccc(C5=CCN(S(=O)(=O)CCC(C)(C)OP(=O)(OCC[Si](C)(C)C)OCC[Si](C)(C)C)CC5)cc4s3)CC2)nc1 | null | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | 25 | null | To a solution of 2-methyl-4-(4-(2-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)benzo[d]thiazol-6-yl)-5,6-dihydropyridin-1(2H)-ylsulfonyl)butan-2-yl bis(2-(trimethylsilyl)ethyl) phosphate (85 mg, 0.098 mmol) in CH2Cl2 (511 μl) at 0° C. was added TFA (51.1 μl, 0.663 mmol). The mixture was stirred and gradually warmed to ... | CCCc1cnc(N2CCC(Oc3nc4ccc(C5=CCN(S(=O)(=O)CCC(C)(C)OP(=O)(O)O)CC5)cc4s3)CC2)nc1 | null | 80.6 | null |
642,879 | ord_dataset-ce71a906ea9c4399a2014cbaaff88c8f | null | 2004-01-01T00:07:00 | true | [C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][C:4]([S:7]([NH:10][CH:11]([CH2:16][CH:17]2[O:19][CH2:18]2)[C:12]([O:14]C)=[O:13])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[C:26]1(C2C=CC=CC=2)[CH:31]=[CH:30][C:29]([S:32](NC(CC=C)C(OC)=O)(=O)=O)=[CH:28][CH:27]=1.O.ClC1C=CC=C(C(OO)=O)C=1>C(Cl)Cl.C([O-])(O)=O.[Na+... | COC(=O)C(CC1CO1)NS(=O)(=O)c1ccc(-c2ccccc2)cc1 | C=CCC(NS(=O)(=O)c1ccc(-c2ccccc2)cc1)C(=O)OC | null | O=C(OO)c1cccc(Cl)c1 | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | ClCCl | null | null | null | null | null | null | null | null | null | null | 8 | Methyl 2-[[(1,1′-biphenyl)-4-yl]sulfonyl]amino-4,5-epoxypentanoate: To a solution of methyl 2-[[(1,1′-biphenyl)-4-yl]sulfonyl]amino-4-pentenoate 16a (2.0 g, 5.8 mmol) in CH2Cl2 (15 mL), NaHCO3 (0.58 g, 7 mmol) and water (10 mL) at 0° C., is added slowly m-chloroperbenzoic acid (3.3 g, 11.6 mmol, 57-86%). The reaction m... | O=C(O)C(CC(O)CSc1ccccc1)NS(=O)(=O)c1ccc(-c2ccccc2)cc1 | null | null | null |
478,044 | ord_dataset-21c1b1c06c7e4e09a38b5b1c71a32e52 | null | 2000-01-01T00:10:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH2:13][CH2:12][CH2:11][C:10]=2[C:14]#[N:15])=[CH:4][CH:3]=1>[Ti](Cl)(Cl)(Cl)Cl.[OH-].[Na+]>[NH2:15][C:14]1[C:4]2[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=2[N:8]=[C:9]2[CH2:13][CH2:12][CH2:11][C:10]=12 | N#CC1=C(Nc2ccc(Cl)cc2)CCC1 | null | null | Cl[Ti](Cl)(Cl)Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 140 | null | Under nitrogen, titanium tetrachloride (1.2 ml, 11 mmol) was added to the above enamine (Example 14) (2.2 g, 10 mmol) and the stirred mixture was heated at 140° C. for 1 hour. After cooling, 10M-sodium hydroxide solution (20 ml) was added and the mixture heated under reflux for 1 hour. After being allowed to cool, this... | Nc1c2c(nc3ccc(Cl)cc13)CCC2 | null | null | null |
553,607 | ord_dataset-ec9decb576c4424c9685993f6262bd9c | null | 2002-01-01T00:07:00 | true | C([O:3][C:4](=[O:40])[C:5]([CH3:39])([O:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][C:17]2[N:18]=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]4[C:38]5[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=5)[CH:32]=[CH:31][CH:30]=4)[CH:24]=3)[O:20][C:21]=2[CH3:22])=[CH:10][CH:9]=1)[CH3:6])C.[OH-].[Na+].Cl.C(OCC)(=O)C>C(O)... | CCOC(=O)C(C)(C)Oc1ccc(OCCc2nc(-c3cccc(-c4cccc5ccccc45)c3)oc2C)cc1 | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CCO | null | null | null | null | null | null | null | null | null | 25 | null | A stirred solution of 2-methyl-2-(4-{2-[5-methyl-2-(3-naphthalen-1-ylphenyl)oxazol-4-yl]ethoxy}phenoxy)propionic acid ethyl ester (0.711 mmol) in ethanol (8.9 mL) was treated with NaOH(aq) (0.854 mL of a 5M solution), and heated at reflux for 1 h. The hot solution was acidified to pH 1 with 1M HCl (6 mL). The mixture w... | Cc1oc(-c2cccc(-c3cccc4ccccc34)c2)nc1CCOc1ccc(OC(C)(C)C(=O)O)cc1 | null | null | null |
1,100,829 | ord_dataset-af85e6f81c2d49f08086afd6d9e6959c | null | 2011-01-01T00:10:00 | true | C(O[C:6]([NH:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=2)[NH:13][CH:12]=1)=O)(C)(C)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:6][NH:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=2)[NH:13][CH:12]=1 | CC(C)(C)OC(=O)NCCc1c[nH]c2cc(Cl)ccc12 | null | null | [Al+3] | [H-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 2 | Combine N-t-butoxycarbonyl-2-(6-chloro-1H-indol-3-yl)ethylamine (1.3 g, 4.41 mmol) and dry THF (20 ml) and add dropwise to an ice bath cooled suspension of LiAlH4 (1.0 g, 26.5 mmol) in dry THF (30 ml). Heat to reflux. After 2 hours, cool to, ambient temperature and stir. After 15 hours, quench with saturated NaSO4 (100... | CNCCc1c[nH]c2cc(Cl)ccc12 | null | null | null |
1,209,841 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | Cl[CH2:2][C:3]([N:5]([O:7][CH3:8])[CH3:6])=[O:4].[Br:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([O:17][CH3:18])[CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(Cl)Cl>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:2][C:3]([N:5]([O:7][CH3:8])[CH3:6])=[O:4])=[C:12]([O:17][CH3:18])[CH:11]=1 | CON(C)C(=O)CCl | COc1cc(Br)ccc1O | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | ClCCl | null | null | null | null | null | null | null | null | null | 60 | 16 | A mixture of 2-chloro-N-methoxy-N-methylacetamide (2.7 g, 19.63 mmol), 4-bromo-2-methoxyphenol (3.98 g, 19.63 mmol), and potassium carbonate (5.43 g, 39.3 mmol) in DMF (20 mL) was heated at 60° C. for 1 hour and stirred at RT overnight (16 hours). The reaction mixture was diluted with CH2Cl2, washed with sat NaHCO3, br... | COc1cc(Br)ccc1OCC(=O)N(C)OC | null | 81.4 | null |
1,483,595 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [CH:1]1([CH2:4][O:5][C:6]2[CH:27]=[CH:26][C:9]([C:10]([N:12]([C@H:14]3[CH2:23][CH2:22][C:21]4[C:16](=[CH:17][CH:18]=[C:19]([CH:24]=O)[CH:20]=4)[CH2:15]3)[CH3:13])=[O:11])=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.C1COCC1.[O:33]1[CH2:38][CH2:37][CH:36]([CH2:39][NH2:40])[CH2:35][CH2:34]1.C([BH3-])#N.[Na+]>C(O)(=O)C>[CH:1]1([CH2:4][... | CN(C(=O)c1ccc(OCC2CC2)cc1)[C@H]1CCc2cc(C=O)ccc2C1 | NCC1CCOCC1 | null | [BH3-]C#N | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 12 | To a mixture of 4-cyclopropylmethoxy-N—((S)-6-formyl-1,2,3,4-tetrahydronaphthalen-2-yl)-N-methylbenzamide (0.20 g), THF (5 ml), C-(tetrahydropyran-4-yl)methylamine (63 mg) and acetic acid (33 mg) was added polymer-bound sodium cyanoborohydride (0.55 mmol), and the suspension was shaken at room temperature for 12 hours.... | CN(C(=O)c1ccc(OCC2CC2)cc1)[C@H]1CCc2cc(CNCC3CCOCC3)ccc2C1 | null | null | null |
1,262,456 | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | null | 2013-01-01T00:02:00 | true | Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[C:14]([Cl:19])=[CH:13][C:12]=2[F:20])[CH2:7][C@@H:6]1[CH3:21])=[O:4].[I:22][C:23]1[C:31]2[C:26](=[N:27][CH:28]=[CH:29][CH:30]=2)[NH:25][N:24]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>C(OCC)(=O)C>[Cl:19][C:14]1[C:15]([O:17][CH3:18])=[CH:16][C:11... | Ic1n[nH]c2ncccc12 | COc1cc(N2CCN(C(=O)CCl)[C@@H](C)C2)c(F)cc1Cl | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 90 | 8 | A mixture of 2-Chloro-1-[(S)-4-(4-chloro-2-fluoro-5-methoxy-phenyl)-2-methyl-piperazin-1-yl]-ethanone (1.37 g, 4.08 mmol, 1 eq), 3-Iodo-1H-pyrazolo[3,4-b]pyridine (1.0 g, 4.08 mmol, 1 eq), potassium carbonate (2.26 g, 16.4 mmol, 4 eq), and DMF (15 ml) was stirred overnight at 90° C. The reaction solution was diluted wi... | COc1cc(N2CCN(C(=O)Cn3nc(I)c4cccnc43)[C@@H](C)C2)c(F)cc1Cl | null | 99.2 | null |
598,452 | ord_dataset-843ef38b45484f72826f5f39d8a29c4d | null | 2003-01-01T00:06:00 | true | C([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH:13]=[CH2:14])[CH:6]=1)(=O)C.[OH-].[Na+].CO>C1COCC1>[CH2:12]([O:11][C:7]1[CH:6]=[C:5]([OH:4])[CH:10]=[CH:9][CH:8]=1)[CH:13]=[CH2:14] | C=CCOc1cccc(OC(C)=O)c1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 1 | The product from Example 61A (7.19 g, 37.4 mmoles) in THF (30 mL) was treated with 4N NaOH (19 mL, 75 mmoles) and MeOH (5 mL). After one hour, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with aqueous NH4Cl, brine, dried (Na2SO4), filtered, and the fil... | C=CCOc1cccc(O)c1 | null | null | null |
49,782 | ord_dataset-0bb2e99daa66408fb8dbd6a0781d241c | null | 1978-01-01T00:12:00 | true | C([O:3][C:4]([C:6]1[N:11](CCC)[C:10]2[CH:15]=[CH:16][C:17](=[O:24])[C:18]([O:20][CH2:21][CH2:22][CH3:23])=[CH:19][C:9]=2[C:8](=[O:25])[CH:7]=1)=[O:5])C.Cl.C>>[O:25]=[C:8]1[CH:7]=[C:6]([C:4]([OH:5])=[O:3])[NH:11][C:10]2[CH:15]=[CH:16][C:17](=[O:24])[C:18]([O:20][CH2:21][CH2:22][CH3:23])=[CH:19][C:9]1=2 | CCCOc1cc2c(=O)cc(C(=O)OCC)n(CCC)c2ccc1=O | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 25 | null | A mixture of 4,7-dihydro-4,7-dioxo-6-propoxy-1-propyl-1H-cyclohepta[b]pyridine-2-carboxlic acid ethyl ester (3.8 g, described in Example 22) and 19% hydrochloric acid (113 ml) is refluxed for 30 minutes. Charcoal is added and the hot mixture is filtered. The filtrate is cooled to room temperature and the crystalline pr... | CCCOc1cc2c(=O)cc(C(=O)O)[nH]c2ccc1=O | null | null | null |
100,616 | ord_dataset-e984b2d4813f44d59867e1771acc9b66 | null | 1982-01-01T00:11:00 | true | CO[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][C:11](C)([OH:19])CC1CCCCN1.Br>C(O)(=O)C>[O:19]1[C:3]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:9][CH2:10][CH2:11]1 | COc1ccccc1CCC(C)(O)CC1CCCCN1 | null | null | Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | Mother liquors made as in part (a), (24 g) are taken up in 200 ml of glacial acetic acid and treated with 100 ml of 48% HBr. After refluxing for 3 hours under nitrogen the mixture is evaporated to an oil, basified (sodium hydroxide), extracted with chloroform, dried (potassium carbonate) and evaporated to 20 g of oil. ... | c1ccc2c(c1)CCCO2 | null | null | null |
201,610 | ord_dataset-31f00a039ca0424788e5e1970d25a8fd | null | 1989-01-01T00:12:00 | true | [O:1]=[C:2]1[N:7]2[N:8]=[CH:9][C:10]3[CH:14]=[CH:13][S:12][C:11]=3[C:6]2=[C:5]([C:15]([O:17][CH3:18])=[O:16])[CH:4]=[C:3]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:25]([BH3-])#N.[Na+]>C(O)=O.O1CCCC1>[CH3:25][N:8]1[CH2:9][C:10]2[CH:14]=[CH:13][S:12][C:11]=2[C:6]2=[C:5]([C:15]([O:17][CH3:18])=[O:16])[CH:4]=[C:3](... | COC(=O)c1cc(-c2ccccc2)c(=O)n2ncc3ccsc3c12 | [BH3-]C#N | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | O=CO | null | null | null | null | null | null | null | null | null | 25 | 24 | 0.34 g of methyl 7-oxo-8-phenyl-7H-pyrido[1,2-b]thieno[2,3-d]pyridazine-10-carboxylate in 10 ml of formic acid are treated dropwise under argon at 25°-30° with 0.31 g of sodium cyanoborohydride in 2 ml of tetrahydro-furan. The mixture is left to stir at room temperature for 24 hours. The solution is poured into 50 ml o... | COC(=O)c1cc(-c2ccccc2)c(=O)n2c1-c1sccc1CN2C | null | null | null |
1,586,671 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | [N+:1]([C:4]1[CH:5]=[N:6][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:8]=1)([O-])=O>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[N:6][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:8]=1 | CC(C)(C)OC(=O)n1cc([N+](=O)[O-])cn1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | tert-butyl 4-nitro-1H-pyrazole-1-carboxylate was stirred with palladium on carbon (10%, 170 mg) in ethanol (20 mL) under an atmosphere of hydrogen at 20° C. for 18 h. The palladium was removed by filtration and the solvent was removed in vacuo to give tert-butyl 4-amino-1H-pyrazole-1-carboxylate (1.48 g). 1H NMR (d6-DM... | CC(C)(C)OC(=O)n1cc(N)cn1 | null | null | null |
979,067 | ord_dataset-f886e51ba1484c76a94bce1482f1eab9 | null | 2010-01-01T00:07:00 | true | [F:1][C:2]1[C:7]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+].I[CH2:25][CH2:26][CH3:27].O>C(#N)C>[F:1][C:2]1[C:7]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:12]1[CH2:17][CH2:16][N:15]([CH2:25][CH2:26][CH3:27])[CH2... | CS(=O)(=O)c1cccc(C2CCNCC2)c1F | CCCI | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC#N | null | null | null | null | null | null | null | null | null | 25 | null | To a solution of 4-[2-fluoro-3-(methylsulfonyl)phenyl]piperidine (0.4 g, 1.55 mmol) in acetonitrile (40 ml) was added potassium carbonate (0.3 g, 2.17 mmol) and 1-iodopropane (0.151 ml, 1.55 mmol) and the mixture was heated at reflux for 15 h. The mixture was cooled to ambient temperature and water (50 ml) was added. T... | CCCN1CCC(c2cccc(S(C)(=O)=O)c2F)CC1 | null | 79.7 | null |
922,913 | ord_dataset-cc0899cd744f4f7f8e7f2463560faad1 | null | 2009-01-01T00:12:00 | true | Cl[C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[C:6]([Cl:13])[C:3]=1[C:4]#[N:5].[CH3:14][NH2:15]>C(OCC)(=O)C>[Cl:13][C:6]1[C:3]([C:4]#[N:5])=[C:2]([NH:15][CH3:14])[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=1 | CN | N#Cc1c(Cl)ccc([N+](=O)[O-])c1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | 5 | 3 | To a 1 L two-neck round bottom flask was added 2,6-dichloro-3-nitrobenzonitrile (11.1 g, 51.1 mmol) followed by ethyl acetate (102 mL). The flask was equipped with an internal thermometer and magnetic stir bar and cooled to 5° C. by immersion into an ice bath. Methylamine was added dropwise to the cooled reaction mixtu... | CNc1c([N+](=O)[O-])ccc(Cl)c1C#N | null | 96 | null |
546,795 | ord_dataset-d31180f42ced44719fd9e72685c798bf | null | 2002-01-01T00:05:00 | true | [C:1]1(/[CH:7]=[C:8](\[C:11]#[C:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]#[CH:18])/[CH:9]=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO.[OH-].[Na+]>[C:1]1(/[CH:7]=[C:8](\[C:11]#[C:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]#[CH:18])/[CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1 | C#CCCCCC#C/C(C=O)=C\c1ccccc1 | null | null | [BH4-] | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 0.5 | To a solution of Compound 2 (502 mg, 2.13 mmol) in methanol (20 mL) was added a solution of NaBH4 (80.4 mg, 2.13 mmol) in aqueous NaOH (0.5 N, 5 mL) followed by stirring at room temperature for 30 minutes. The reaction was then quenched with saturated aqueous NH4Cl (50 mL) and extracted with EtOAc (50 mL×2). The combin... | C#CCCCCC#C/C(=C\c1ccccc1)CO | null | 91.1 | null |
696,356 | ord_dataset-a7baa616c65d42559e25ca0ba61e0744 | null | 2006-01-01T00:01:00 | true | [C:1]1([PH:7](=[O:14])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1COCC1.[CH3:20][C:21]([CH3:23])=[O:22]>>[C:1]1([P:7]([C:21]([OH:22])([CH3:23])[CH3:20])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:14])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1 | O=[PH](c1ccccc1)c1ccccc1 | CC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 70 | null | To a one liter four-inlet flask equipped with a temperature controller, a reflux condenser, a nitrogen feed and a mechanical stirrer, 1 mole (202 g) diphenyl phosphine oxide (DPPO) and 500 ml THF were added. The mixture was heated to 70° C. and then stirred. The stirring was continued until DPPO was dissolved completel... | CC(C)(O)P(=O)(c1ccccc1)c1ccccc1 | null | null | null |
1,544,947 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [F:1][C:2]([F:23])([F:22])[C:3]1[N:7]2[CH:8]=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([OH:21])([CH3:20])[CH3:19])=[CH:14][CH:13]=3)[CH:10]=[CH:11][C:6]2=[N:5][N:4]=1.[H-].[Na+].[CH3:26]I>C1COCC1>[CH3:26][O:21][C:18]([C:15]1[CH:16]=[CH:17][C:12]([C:9]2[CH:10]=[CH:11][C:6]3[N:7]([C:3]([C:2]([F:1])([F:22])[F:23])=[N:4][N... | CC(C)(O)c1ccc(-c2ccc3nnc(C(F)(F)F)n3c2)cc1 | CI | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 8 | In a 10-mL cone-shaped flask equipped with a magnetic stir bar 2-(4-(3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)phenyl)propan-2-ol (28 mg) was dissolved in dry THF (1 mL) and NaH (60% suspension in mineral oil, 20 eq.) and MeI (50 eq.) were added. The reaction mixture was stirred overnight at room temperatu... | COC(C)(C)c1ccc(-c2ccc3nnc(C(F)(F)F)n3c2)cc1 | null | null | null |
1,736,217 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | [F:1][CH:2]([F:11])[O:3][C:4]1[C:5]([NH2:10])=[N:6][CH:7]=[CH:8][CH:9]=1.[Br:12]N1C(=O)CCC1=O>C(#N)C>[Br:12][C:8]1[CH:9]=[C:4]([O:3][CH:2]([F:1])[F:11])[C:5]([NH2:10])=[N:6][CH:7]=1 | Nc1ncccc1OC(F)F | O=C1CCC(=O)N1Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | null | 0.33 | To a solution of 3-(difluoromethoxy)pyridin-2-amine (2.3 g, 14.36 mmol) in acetonitrile (15 mL) was added N-bromosuccinimide (2.61 g, 14.65 mmol) over 3 min at 0° C. The reaction mixture was stirred at the same temperature for another 20 min and subsequently concentrated to dryness in vacuo. The resulting viscous mass ... | Nc1ncc(Br)cc1OC(F)F | null | 93.2 | null |
1,027,900 | ord_dataset-83acb82dc5ba4f7aba439b9875aaac43 | null | 2011-01-01T00:02:00 | true | F[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH3:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C([O-])(O)=O.[Na+]>C1COCC1>[CH3:15][N:16]1[CH2:21][CH2:20][N:19]([C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=2[N+:12]([O-:14])=[O:13])[CH2:18][CH2:17]1 | O=[N+]([O-])c1cc(C(F)(F)F)ccc1F | CN1CCNCC1 | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | null | Example 18 was prepared in accordance to a procedure described in Collins, et. al., Tetrahedron, 48, No. 37, pp 7887-7898, 1992. To a solution of 1-Fluoro-2-nitro-4-trifluoromethyl-benzene (1.0 g, 4.78 mmol) in dry THF (24 mL) was added 1-Methyl-piperazine (0.64 mL, 5.74 mmol). The solution turned bright yellow. NaHCO3... | CN1CCN(c2ccc(C(F)(F)F)cc2[N+](=O)[O-])CC1 | null | null | null |
1,319,029 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | Br[CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCl>[C:6]1([CH:2]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:3]([OH:5])=[O:4])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1 | O=C(O)C(Br)c1ccccc1 | Nc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | null | α-Bromophenylacetic acid (5.01 g, 23.2 mmol) was dissolved in aniline (25 ml, 274 mmol), and the mixture reacted in a closed vessel under microwave irradiation at 120° C. for 5 minutes (UPLC-MS monitoring: complete conversion). Dichloromethane (DCM) (100 ml) was added to the reaction mixture, and the resulting solid wa... | O=C(O)C(Nc1ccccc1)c1ccccc1 | null | 97 | null |
644,086 | ord_dataset-c975a50a7600448fabd558f4a94a3e29 | null | 2004-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[N:13]=[C:12]([C:14]2[C:18]([CH3:19])=[CH:17][S:16][CH:15]=2)[N:11]([CH3:20])[N:10]=1.[Br:21]Br.O>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[N:13]=[C:12]([C:14]2[C:18]([CH3:19])=[C:17]([Br:21])[S:16][CH:15]=2)[N:11]([CH3:20])[N:10]=1 | BrBr | Cc1cscc1-c1nc(-c2c(F)cccc2Cl)nn1C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | O | null | null | null | null | null | null | null | null | null | 45 | 14 | A suspension of 3-(2-chloro-6-fluorophenyl)-1-methyl-5-(4-methylthien-3-yl)-1H-1,2,4-triazole (2.35 g, 7.6 mmol) in glacial acetic acid (15 mL) was heated to 45° C. in order to effect solubilization. After cooling to 10° C., a solution of bromine (1.34 g, 0.43 mL, 8.4 mmol) in glacial acetic acid (4 mL) was added and t... | Cc1c(-c2nc(-c3c(F)cccc3Cl)nn2C)csc1Br | null | null | null |
963,444 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | C([O:3][C:4](=[O:35])[CH2:5][CH2:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([CH2:14][CH2:15][C:16]([C:18]2[S:19][C:20]([C:29]([F:32])([F:31])[F:30])=[C:21]3[CH2:26][C:25]([CH3:28])([CH3:27])[CH2:24][CH2:23][C:22]=23)=[O:17])=[CH:9][C:8]=1[CH2:33][CH3:34])C>C1COCC1.CO.[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH3:28][C:25]1... | CCOC(=O)CCc1c(C)cc(CCC(=O)c2sc(C(F)(F)F)c3c2CCC(C)(C)C3)cc1CC | null | null | O=C(O)CC(O)(CC(=O)O)C(=O)O | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CO | null | null | null | null | null | null | null | null | null | null | null | A solution of 3-{4-[3-(5,5-dimethyl-3-trifluoromethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propyl]-2-ethyl-6-methyl-phenyl}-propionic acid ethyl ester (340 mg, 0.668 mmol) in THF (5 mL), methanol (4 mL) and 2 N aq. LiOH (2 mL) is stirred at rt for 2 h before it is diluted with 10% aq. citric acid solution an... | CCc1cc(CCC(=O)c2sc(C(F)(F)F)c3c2CCC(C)(C)C3)cc(C)c1CCC(=O)O | null | 64.2 | null |
199,396 | ord_dataset-aa9e93ade540499c920a9c3b18e8edaa | null | 1989-01-01T00:11:00 | true | COC1C=CC(C(C2C=CC(OC)=CC=2)[N:10]2[CH2:14][C@@H:13]3[O:15][C:16]4[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][CH:20]=[CH:19][C:17]=4[O:18][C@H:12]3[CH2:11]2)=CC=1.Cl.O.C(Cl)(Cl)[Cl:37]>C(O)=O>[ClH:37].[N+:23]([C:22]1[C:16]2[O:15][C@@H:13]3[C@H:12]([CH2:11][NH:10][CH2:14]3)[O:18][C:17]=2[CH:19]=[CH:20][CH:21]=1)([O-:25])=[O:... | ClC(Cl)Cl | COc1ccc(C(c2ccc(OC)cc2)N2C[C@@H]3Oc4cccc([N+](=O)[O-])c4O[C@H]3C2)cc1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | O=CO | null | null | null | null | null | null | null | null | null | null | null | A solution of (±)-(trans)-2-[bis(4-methoxyphenyl)methyl]-2,3,3a,9a-tetrahydro-5-nitro-1H-[1,4]benzodioxino[2,3-c]pyrrole (1.12 g) in formic acid (10 ml) was heated under reflux with 10M hydrochloric acid (0.5 ml), water (1 ml) and chloroform (5 ml) for 70 minutes. The maroon mixture was cooled and partitioned between c... | O=[N+]([O-])c1cccc2c1O[C@H]1CNC[C@@H]1O2 | null | null | null |
1,113,204 | ord_dataset-375a420ee9b042918ddca20f02df37d3 | null | 2011-01-01T00:11:00 | true | [NH:1]1[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1.[Cl:7][CH2:8][CH2:9][CH2:10]I.Cl>C1COCC1.CCOCC.[Zn]>[ClH:7].[Cl:7][CH2:8][CH2:9][CH2:10][N:1]1[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1 | C1CSCCN1 | ClCCCI | null | Cl | [Zn] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCOCC | null | null | null | null | null | null | null | null | null | 25 | 8 | Step 1. To a solution of thiomorpholine (1.0 g, 9.7 mmol) and 1-chloro-3-iodopropane (1.98 g, 9.7 mmol) in dry THF (30 ml) was added activated zinc powder (0.64 g, 9.7 g atom). After the mixture was stirred at rt overnight, it was filtered, washed with EtOAc (20 ml), and concentrated. The residue was dissolved in EtOAc... | ClCCCN1CCSCC1 | null | 38.2 | null |
820,006 | ord_dataset-ec58fad8331a42c5a67ad75aac6713b4 | null | 2008-01-01T00:05:00 | true | C([O:8][C:9]1[CH:13]=[C:12](/[CH:14]=[CH:15]/[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[N:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:10]=1)C1C=CC=CC=1>[Pd].O1CCCC1>[C:22]1([N:11]2[C:12](/[CH:14]=[CH:15]/[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:13][C:9]([OH:8])=[N:10]2)[CH:23]=[CH:24][CH:25]=[CH... | C(=C/c1cc(OCc2ccccc2)nn1-c1ccccc1)\c1ccccn1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | 2-[(E)-2-(3-Benzyloxy-1-phenyl-1H-pyrazol-5-yl)ethenyl]pyridine (2.52 g), 5% palladium on carbon (3.0 g) and tetrahydrofuran (200 mL) were subjected to catalytic reduction under a hydrogen atmosphere and atmospheric pressure. The catalyst was filtered off and the filtrate was concentrated to give 1-phenyl-5-[(E)-2-pyri... | Oc1cc(/C=C/c2ccccn2)n(-c2ccccc2)n1 | null | 79.9 | null |
1,657,088 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [N+:1]([C:4]1[C:5]([NH:13][C@H:14]2[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]2)=[C:6]2[S:12][CH:11]=[CH:10][C:7]2=[N:8][CH:9]=1)([O-])=O>[Pd].CO>[NH2:1][C:4]1[C:5]([NH:13][C@H:14]2[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])... | CC(C)(C)OC(=O)N1CCC[C@H](Nc2c([N+](=O)[O-])cnc3ccsc23)C1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | 8 | A mixture of tert-butyl (3S)-3-[(6-nitrothieno[3,2-b]pyridin-7-yl)amino]piperidine-1-carboxylate (0.26 g, 0.69 mmol) and 10% palladium on carbon (80 mg) in methanol (5.0 mL) was stirred under an atmosphere of H2 (balloon) overnight. The mixture was filtered through a pad of Celite and concentrated to give 0.24 g of the... | CC(C)(C)OC(=O)N1CCC[C@H](Nc2c(N)cnc3ccsc23)C1 | null | 99.8 | null |
229,453 | ord_dataset-9adbd9cd2fd941f7af27fb31c9bf3bac | null | 1991-01-01T00:06:00 | true | [CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].[OH-].[Na+].Cl[CH2:13][CH2:14][OH:15]>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH2:13][CH2:14][OH:15] | COc1ccccc1O | OCCCl | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 43.2 g (0.35 mole) of 2-methoxyphenol (guaiacol, Aldrich) in 200 ml of ethanol was stirred and treated with 29 ml (0.36 mole) of 50% sodium hydroxide solution. To this solution was added a solution of 28.2 g (0.35 mole) of 2-chloroethanol (Aldrich) in 50 ml of ethanol and the reaction mixture was heated a... | COc1ccccc1OCCO | null | 41.6 | null |
1,355,554 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | C([O:3][C:4]([C:6]1([NH:15][C:16](=[O:29])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=2[O:24][CH2:25][CH:26]2[CH2:28][CH2:27]2)[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])C.[OH-].[K+].O>CCO>[CH:26]1([CH2:25][O:24][C:18]2[C:19]([CH3:23])=[CH:20][CH:21]=[CH:22][C:17]=2[C:16]([NH:15][C:6]... | CCOC(=O)C1(NC(=O)c2cccc(C)c2OCC2CC2)Cc2ccccc2C1 | null | null | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCO | null | null | null | null | null | null | null | null | null | 25 | 8 | The mixture of 2-(2-cyclopropylmethoxy-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (10) (240 mg, 0.61 mmol) and KOH (500 mg, 8.93 mmol) is dissolved in EtOH (6 mL) and water (1 mL) under a water bath. The water bath is removed when KOH is completely dissolved and the resulting reaction solution is stirre... | Cc1cccc(C(=O)NC2(C(=O)O)Cc3ccccc3C2)c1OCC1CC1 | null | 100 | null |
724,919 | ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | null | 2006-01-01T00:08:00 | true | [C:1]1([CH:7]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:8][NH:9][C:10]2[N:18]=[C:17]([C:19]([OH:21])=O)[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][N:14]3[C@H:22]2[C@H:26]([OH:27])[C@H:25]([OH:28])[C@@H:24]([C:29]([NH:31][CH2:32][CH3:33])=[O:30])[O:23]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:40][C:41]([F:52])([F:51])[... | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)O)nc32)[C@H](O)[C@@H]1O | O=C(NC1CCNCC1)C(F)(F)F | null | CCN=C=NCCCN(C)C | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | null | A solution of 6-[(2,2-diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-9H-purine-2-carboxylic acid (Preparation 39) (0.2 g, 0.38 mmol), 2,2,2-trifluoro-N-(4-piperidinyl)acetamide (83 mg, 0.42 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (81 mg, 0... | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)N4CCC(NC(=O)C(F)(F)F)CC4)nc32)[C@H](O)[C@@H]1O | null | null | null |
1,551,772 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | Br[C:2]1[C:3]2[C:4]3[CH:17]=[CH:16][S:15][C:5]=3[C:6](=[O:14])[NH:7][C:8]=2[CH:9]=[CH:10][C:11]=1[O:12][CH3:13].CC1(C)C(C)(C)OB(/[CH:26]=[CH:27]/[CH2:28][N:29]2[CH2:34][CH2:33][CH:32]([NH:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])[CH2:31][CH2:30]2)O1>>[CH3:13][O:12][C:11]1[CH:10]=[CH:9][C:8]2[NH:7][C:6... | COc1ccc2[nH]c(=O)c3sccc3c2c1Br | CC(C)(C)OC(=O)NC1CCN(C/C=C/B2OC(C)(C)C(C)(C)O2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (180 mg, 0.48 mmol) was reacted with (E)-tert-butyl 1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl]piperidin-4-ylcarbamate (100 mg, 0.32 mmol) to afford the desired product (86 mg, 57%) as a brown solid: ESI MS m/z 470 [C25H31N3O4S... | COc1ccc2[nH]c(=O)c3sccc3c2c1/C=C/CN1CCC(NC(=O)OC(C)(C)C)CC1 | null | 57.2 | null |
1,409,305 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | [CH:1]1([C:4]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[C:5]=2[C:6](OC)=[O:7])[CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH:1]1([C:4]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[C:5]=2[CH2:6][OH:7])[CH2:3][CH2:2]1 | COC(=O)c1c(F)cccc1C1CC1 | null | null | [Al+3] | [H-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | O | null | null | null | null | null | null | null | null | null | 0 | 8 | To a solution of methyl 2-cyclopropyl-6-fluorobenzoate (3, 4.54 g, 23.4 mmol) in anhydrous tetrahydrofuran (30 mL) at room temperature was added lithium aluminium hydride (1.42 g, 37.4 mmol) in small portions and the mixture was stirred overnight. The reaction mixture was cooled to 0° C. and water (3 mL) was added drop... | OCc1c(F)cccc1C1CC1 | null | 84.6 | null |
1,182,125 | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | null | 2012-01-01T00:07:00 | true | [OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH:12]1([CH:15](O)[CH3:16])[CH2:14][CH2:13]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[CH:12]1([CH:15]([O:1][C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])[CH3:16])[CH2:14][CH2:13]1 | CC(O)C1CC1 | COC(=O)c1cccc(O)c1 | null | CC(C)OC(=O)/N=N/C(=O)OC(C)C | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 25 | null | Methyl 3-hydroxybenzoate (10.0 g, 65.7 mmol) in toluene (65.7 ml) was cooled to 0° C. and added 1-cyclopropylethanol (6.43 ml, 65.7 mmol), triphenylphosphine (18.9 g, 72.3 mmol), and DIAD (14.1 ml, 72.3 mmol). The reaction warmed to rt for sixteen hours. The reaction mixture was filtered through a fritted funnel to rem... | COC(=O)c1cccc(OC(C)C2CC2)c1 | null | null | null |
169,933 | ord_dataset-37d3220f708c49ad839bab296b722248 | null | 1988-01-01T00:03:00 | true | [H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.Cl[CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1>CN(C)C=O>[Br:3][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[O:10][CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1 | ClCc1ccc2ccccc2n1 | Oc1cccc(Br)c1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 8 | To 60% sodium hydride (9.8 g, 245 mmol) in 250 mL dimethylformamide at 5° C. under nitrogen is added portionwise 3-bromophenol (42.6 g, 246 mmol). After thirty minutes a solution of 2-(chloromethyl)quinoline (43.6 g, 246 mmol) in 250 mL dimethylformamide is rapidly added. The reaction is allowed to warm to room tempera... | Brc1cccc(OCc2ccc3ccccc3n2)c1 | null | 55.4 | null |
409,489 | ord_dataset-324fb6fdc2414cb79e436bf5d04d4bd2 | null | 1998-01-01T00:08:00 | true | C([O:8][C:9]1[CH:10]=[C:11]([O:16][S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)(=[O:19])=[O:18])[CH:12]=[C:13]([CH3:15])[CH:14]=1)C1C=CC=CC=1>[Pd].C(O)C>[OH:8][C:9]1[CH:10]=[C:11]([O:16][S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:27])[F:28])[CH:21]=2)(=[O:19])=[O:... | Cc1cc(OCc2ccccc2)cc(OS(=O)(=O)c2cccc(C(F)(F)F)c2)c1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 3-trifluoromethylbenzenesulfonic acid 3-benzyloxy-5-methylphenyl ester (633 mg, 1.5 mmol), as prepared in the preceding step, and 10% palladium on carbon (100 mg) in ethanol (20 mL) was hydrogenated (balloon) for 3 h. The catalyst was removed by filtration through diatomaceous earth (methanol washes) and t... | Cc1cc(O)cc(OS(=O)(=O)c2cccc(C(F)(F)F)c2)c1 | null | 97.3 | null |
1,041,934 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | Cl[C:2]1[S:6][C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([SH:22])=[CH:18][CH:17]=1.C([O-])(=O)C.[Na+].C(OCC)C>C(O)C>[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([S:22][C:2]2[S:6][C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:4][C:3]=2[N+:12]([O-:14])=[O:13]... | CCOC(=O)c1cc([N+](=O)[O-])c(Cl)s1 | Nc1ccc(S)cc1 | null | CC(=O)[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | CCO | null | null | null | null | null | null | null | null | null | 25 | null | The product of Example 430A (1.0 g, 4.244 mmol), 4-aminothiophenol (0.797 g, 6.366 mmol), and anhydrous sodium acetate (1.74 g, 21.22 mmol) were heated in anhydrous ethanol (40 mL) under a nitrogen atmosphere at reflux for 30 minutes. The reaction was cooled to room temperature, partitioned with ethyl acetate (100 mL) ... | CCOC(=O)c1cc([N+](=O)[O-])c(Sc2ccc(N)cc2)s1 | null | 84.8 | null |
1,462,873 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | [F:1][C:2]([F:32])([F:31])[C:3]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[CH:23][C:4]=1[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11](/[CH:15]=[C:16]3/[C:17](=[O:22])[NH:18][C:19](=[O:21])[S:20]/3)=[CH:12][CH:13]=2)[CH:8]=[CH:7]1.Cl.[CH3:34][N:35]([CH3:39])[CH2:36][CH2:37]Cl>>[F:32][C:2]([F:1])([F:31])[C:3]1[CH:26... | CN(C)CCCl | O=C1NC(=O)/C(=C/c2ccc3c(ccn3Cc3ccc(C(F)(F)F)cc3C(F)(F)F)c2)S1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | (5Z)-5-[(1-{[2,4-Bis(trifluoromethyl)phenyl]methyl}-1H-indol-5-yl)methylidene]-3-[2-(dimethylamino)ethyl]-1,3-thiazolidine-2,4-dione was prepared from [(5Z)-5-({1-[2,4-bis-(trifluoromethyl)benzyl]-1H-indol-5-yl}methylidene)-2,4-dioxo-1,3-thiazolidine (from Example 238) and 2-(dimethylamino)ethyl chloride hydrochloride ... | CN(C)CCN1C(=O)S/C(=C\c2ccc3c(ccn3Cc3ccc(C(F)(F)F)cc3C(F)(F)F)c2)C1=O | null | null | null |
1,157,099 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | [Cl:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6](Cl)[N:5]=[C:4]([S:11][CH3:12])[N:3]=1.C(N(C(C)C)C(C)C)C.[C:22]([O:26][CH3:27])(=[O:25])[CH2:23][SH:24]>C(Cl)Cl>[CH3:27][O:26][C:22](=[O:25])[CH2:23][S:24][C:6]1[C:7]([CH:8]=[O:9])=[C:2]([Cl:1])[N:3]=[C:4]([S:11][CH3:12])[N:5]=1 | CSc1nc(Cl)c(C=O)c(Cl)n1 | COC(=O)CS | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | ClCCl | null | null | null | null | null | null | null | null | null | 25 | null | To an ice-cooled solution (−10° C.) of 4,6-dichloro-2-methylsulfanyl-pyrimidine-5-carbaldehyde (2.0 g, 8.97 mmol) and iPr2EtN (0.82 mL, 8.97 mmol) in DCM (40 mL) was added methyl thioglycolate (1.56 mL, 8.97 mmol) in DCM (20 mL) over 15 min. The reaction mixture was let warm to RT, then washed with sat. NaHCO3, dried o... | COC(=O)CSc1nc(SC)nc(Cl)c1C=O | null | null | null |
926,477 | ord_dataset-cc0899cd744f4f7f8e7f2463560faad1 | null | 2009-01-01T00:12:00 | true | [NH2:1][C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:11](Cl)(=[O:16])[CH2:12][CH:13]([CH3:15])[CH3:14].O>CN(C=O)C>[CH3:14][CH:13]([CH3:15])[CH2:12][C:11]([NH:1][C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])=[O:16] | Nc1cnccc1C(=O)O | CC(C)CC(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 0 | 2.5 | To a solution of 3-aminoisonicotinic acid 1-1 (3.89 g, 28.16 mmol) in DMF at 0° C. was added isovaleryl chloride (3.73 g, 30.97 mmol) and the reaction was stirred at 0° C. After 2.5 h, water was added to the reaction mixture and a precipitate formed which was collected by filtration and washed with ether to afford the ... | CC(C)CC(=O)Nc1cnccc1C(=O)O | null | null | null |
353,423 | ord_dataset-127eb5fdd5b4402e92b51d0b55a5dcb5 | null | 1997-01-01T00:01:00 | true | [Br:1][C:2]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:8]2[C:3]=1[N:4]=[C:5]([NH2:17])[C:6](=[O:16])[NH:7]2.Cl.N[OH:20].O>C(O)CCC>[Br:1][C:2]1[CH:11]=[C:10]([C:12]([F:14])([F:15])[F:13])[CH:9]=[C:8]2[C:3]=1[NH:4][C:5](=[N:17][OH:20])[C:6](=[O:16])[NH:7]2 | Nc1nc2c(Br)cc(C(F)(F)F)cc2[nH]c1=O | NO | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCCCO | null | null | null | null | null | null | null | null | null | 25 | null | An adaptation of the method of Harsanyi et al., Liebigs Ann. Chem. 190 (1973) was used. A mixture of 5-bromo-7-trifluoromethyl-3-aminoquinoxalin-2(1H)-one (75 mg, 0.24 mmol) and hydroxylamine hydrochloride (38 mg, 0.54 mmol; Aldrich Co.) in 3 mL of 1-butanol was heated to reflux. The resulting suspension was stirred un... | O=c1[nH]c2cc(C(F)(F)F)cc(Br)c2[nH]c1=NO | null | 86.1 | null |
229,557 | ord_dataset-9adbd9cd2fd941f7af27fb31c9bf3bac | null | 1991-01-01T00:06:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:19][CH2:20][CH2:21][C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)[CH:17]=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C1(P(=[CH:47][C:48]([O:50][CH3:51])=[O:49])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:... | O=CC(CCCCNS(=O)(=O)c1ccc(Cl)cc1)CCCc1cccnc1 | COC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | To a solution of 3.08 g (7.5 mmol) of 6-(p-chlorophenylsulfonamido)-2-[3-(3-pyridyl)propyl]-hexanal in 40 mL chloroform is added 2.88 g (8.4 mmol) of methyl (triphenylphosphoranylidene)-acetate and then subjected to reflux for 3 hours. The solvent is evaporated and the residue taken up in ether and extracted with 0.5N ... | COC(=O)C=CC(CCCCNS(=O)(=O)c1ccc(Cl)cc1)CCCc1cccnc1 | null | null | null |
1,446,342 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [CH3:1][N:2]1[C:6]2=[N:7][C:8]([C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[C:13]#[N:14])=[CH:9][CH:10]=[C:5]2[NH:4][C:3]1=[O:19].[C:20]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:25]=[CH:24][CH:23]=[C:22](B(O)O)[CH:21]=1.C(N(CC)CC)C>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:20]1([C:29]2[CH:30]=[CH:31][CH:3... | Cn1c(=O)[nH]c2ccc(-c3ccccc3C#N)nc21 | OB(O)c1cccc(-c2ccccc2)c1 | null | [Cu+2] | CC(=O)[O-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | null | 96 | To a solution of 4-1 (13 mg, 0.052 mmol) in DCM (0.25 mL) was added copper (II) acetate, biphenyl-3-ylboronic acid (30 mg, 0.16 mmol) and triethylamine (0.022 mL, 16 mg, 0.16 mmol) at room temperature. After 4 days, the crude mixture was diluted in DCM (4 mL), filtered, concentrated and purified via reverse phase chrom... | Cn1c(=O)n(-c2cccc(-c3ccccc3)c2)c2ccc(-c3ccccc3C#N)nc21 | null | null | null |
90,184 | ord_dataset-aeb5378e6e67443e8a4f5c7a5ec3de51 | null | 1981-01-01T00:12:00 | true | [Br-].[Al+3].[Br-].[Br-].[CH3:5][C:6]12[CH2:14][C:10]1([C:11]([OH:13])=[O:12])[N:9]1[C:15](=[O:27])[CH:16]([NH:17][C:18](=[O:26])[CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C@H:8]1[S:7]2.Cl>C(=S)=S>[CH3:5][CH:6]1[CH:14]=[C:10]([C:11]([OH:13])=[O:12])[N:9]2[C:15](=[O:27])[CH:16]([NH:17][C:18](=[O:26])[CH2:19... | CC12CC1(C(=O)O)N1C(=O)C(NC(=O)Cc3ccccc3)[C@H]1S2 | null | null | Cl | [Al+3] | [Br-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | S=C=S | null | null | null | null | null | null | null | null | null | null | null | 20 | A solution of aluminum bromide (1.7 g.) in carbon disulfide (40 ml.) was dropwise added under stirring at room temperature to a suspension of 2-methyl-2,3-methylene-6-(2-phenylacetamido)penam-3-carboxylic acid (0.66 g.) in carbon disulfide (70 ml.) and the mixture was stirred for 20 hours at the same temperature. After... | CC1C=C(C(=O)O)N2C(=O)C(NC(=O)Cc3ccccc3)[C@H]2S1 | null | 50 | null |
759,881 | ord_dataset-2e58cb8db2bf482bbea23283b7e04488 | null | 2007-01-01T00:03:00 | true | [O:1]1[C:5]2[CH:6]=[CH:7][C:8]([N:10]3[C:18]4[C:17]5[CH:19]=[C:20]([NH:23]C(C6C(Cl)=NC=CC=6)=O)[CH:21]=[CH:22][C:16]=5[CH2:15][CH2:14][C:13]=4[C:12]([C:33]([NH2:35])=[O:34])=[N:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.N>C(O)C>[NH2:23][C:20]1[CH:21]=[CH:22][C:16]2[CH2:15][CH2:14][C:13]3[C:12]([C:33]([NH2:35])=[O:34])=[N:11][N:1... | NC(=O)c1nn(-c2ccc3c(c2)OCO3)c2c1CCc1ccc(NC(=O)c3cccnc3Cl)cc1-2 | null | null | N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 100 | 8 | The title product of Step 3 was dissolved in anhydrous ethanol and then an approximately equal volume of liquid ammonia was added. The resulting mixture was sealed in a pressure vessel and then stirred overnight at 100° C. After cooling, the mixture was concentrated. The residue was taken up in dichloromethane-methanol... | NC(=O)c1nn(-c2ccc3c(c2)OCO3)c2c1CCc1ccc(N)cc1-2 | null | null | null |
1,547,666 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [CH:1](NC(C)C)(C)C.[Li]CCCC.[F:13][C:14]([F:26])([F:25])[CH:15]1[CH2:20][CH2:19][CH:18]([C:21]([O:23][CH3:24])=[O:22])[CH2:17][CH2:16]1.CI>O1CCCC1>[CH3:1][C:18]1([C:21]([O:23][CH3:24])=[O:22])[CH2:17][CH2:16][CH:15]([C:14]([F:25])([F:26])[F:13])[CH2:20][CH2:19]1 | CC(C)NC(C)C | COC(=O)C1CCC(C(F)(F)F)CC1 | null | [Li]CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CI | C1CCOC1 | null | null | null | null | null | null | null | null | null | -78 | 0.33 | To a solution of diisopropylamine (22.0 mL, 124.0 mmol) in tetrahydrofuran (60 mL) was added n-BuLi (2.0 M solution in hexane, 59.0 mL, 95.0 mmol) at 0° C. and the reaction mixture was allowed to stir at same temperature for 20 minutes before cooled to −78° C. Methyl 4-(trifluoromethyl)cyclohexanecarboxylate (10.0 g, 4... | COC(=O)C1(C)CCC(C(F)(F)F)CC1 | null | 104.1 | null |
1,658,233 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | Cl[C:2]1[N:3]=[C:4]2[CH:12]=[CH:11][N:10]=[CH:9][C:5]2=[N:6][C:7]=1[Cl:8].CC[N:15](C(C)C)[CH:16]([CH3:18])[CH3:17].CC(N)C>C(Cl)Cl>[Cl:8][C:7]1[N:6]=[C:5]2[CH:9]=[N:10][CH:11]=[CH:12][C:4]2=[N:3][C:2]=1[NH:15][CH:16]([CH3:18])[CH3:17] | Clc1nc2ccncc2nc1Cl | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CC(C)N | null | null | null | null | null | null | null | null | null | 0 | 0.5 | To a solution of 2,3-dichloropyrido[3,4-b]pyrazine (2.5 g, 12.50 mmol) and DIPEA (6.53 mL, 37.5 mmol) in DCM (25 mL) was added propan-2-amine (1.065 mL, 12.50 mmol) at 0° C. The mixture was stirred at 0° C. for 30 min, warmed slowly to 23° C., and stirred for 12 h. The crude mixture was partitioned between EtOAc (100 m... | CC(C)Nc1nc2ccncc2nc1Cl | null | 65.7 | null |
1,261,894 | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | null | 2013-01-01T00:02:00 | true | B(Br)(Br)Br.[CH2:5]([C:7]1[C:30]([F:31])=[CH:29][C:10]([O:11][C:12]2[CH:27]=[CH:26][C:15]([C:16]([N:18]3[CH2:23][CH2:22][N:21]([CH3:24])[C:20](=[O:25])[CH2:19]3)=[O:17])=[CH:14][C:13]=2[F:28])=[C:9]([O:32]C)[CH:8]=1)[CH3:6].[Cl-].[NH4+]>ClCCl>[CH2:5]([C:7]1[C:30]([F:31])=[CH:29][C:10]([O:11][C:12]2[CH:27]=[CH:26][C:15]... | CCc1cc(OC)c(Oc2ccc(C(=O)N3CCN(C)C(=O)C3)cc2F)cc1F | null | null | BrB(Br)Br | [Cl-] | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 8 | A commercial solution of boron tribromide (1N in DCM, 1.33 mL, 1.32 mmol) was added to a solution of 4-[4-(4-ethyl-5-fluoro-2-methoxyphenoxy)-3-fluorobenzoyl]-1-methylpiperazin-2-one (which may be prepared in accordance with the experimental described in Example 5, step 2; 200 mg, 0.49 mmol) in dichloromethane (1.6 mL)... | CCc1cc(O)c(Oc2ccc(C(=O)N3CCN(C)C(=O)C3)cc2F)cc1F | null | null | null |
1,092,030 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | [N+:1]([C:4]1[C:9]([O:10][C:11]2[CH:12]=[C:13]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[CH:14]=[CH:15][CH:16]=2)=[CH:8][CH:7]=[CH:6][N:5]=1)([O-])=O.[H][H]>C(O)C.[Pd]>[O:20]1[CH2:21][CH2:22][N:17]([C:13]2[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=2)[O:10][C:9]2[C:4]([NH2:1])=[N:5][CH:6]=[CH:7][CH:8]=2)[CH2:18][CH2:19... | [H][H] | O=[N+]([O-])c1ncccc1Oc1cccc(N2CCOCC2)c1 | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | In a 125 mL round-bottom flask, 4-(3-(2-nitropyridin-3-yloxy)phenyl)morpholine (0.92 g, 3.05 mmol) was dissolved in 30 mL of ethanol and 200 mg of 10% Pd/C (Degussa type, 50% wet) added. The resulting mixture was agitated overnight under the atmospheric pressure of hydrogen. The mixture was filtered and the solvent was... | Nc1ncccc1Oc1cccc(N2CCOCC2)c1 | null | 96.7 | null |
762,036 | ord_dataset-2e58cb8db2bf482bbea23283b7e04488 | null | 2007-01-01T00:03:00 | true | O.[OH-].[Li+:3].C[O:5][C:6]([C:8]1[O:9][C:10]2[CH2:11][N:12]([CH3:17])[CH2:13][CH2:14][C:15]=2[N:16]=1)=[O:7]>O1CCCC1>[CH3:17][N:12]1[CH2:13][CH2:14][C:15]2[N:16]=[C:8]([C:6]([O-:7])=[O:5])[O:9][C:10]=2[CH2:11]1.[Li+:3] | COC(=O)c1nc2c(o1)CN(C)CC2 | null | null | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | O | null | null | null | null | null | null | null | null | null | null | 0.17 | Water (6.0 ml) and lithium hydroxide (99.7 mg) were added to a solution of 2-methoxycarbonyl-5-methyl-4,5,6,7-tetrahydrooxazolo[5,4-c]pyridine (800 mg) in tetrahydrofuran (24 ml) at room temperature, and the mixture was stirred for 10 minutes. The reaction mixture was concentrated under reduced pressure to obtain the t... | CN1CCc2nc(C(=O)[O-])oc2C1 | null | 107.6 | null |
1,077,058 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | [F:1][C:2]1[CH:30]=[C:29]([N+:31]([O-])=O)[CH:28]=[CH:27][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[C:11]#[C:12][CH2:13][N:14]1[CH2:17][CH:16]([CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:15]1.[NH4+].[Cl-]>[Fe]>[NH2:31][C:29]1[CH:28]=[CH:27][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C... | CC(C)(C)OC(=O)NCC1CN(CC#Cc2cnccc2Oc2ccc([N+](=O)[O-])cc2F)C1 | null | null | [Fe] | [Cl-] | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared by the reduction of tert-butyl (1-(3-(4-(2-fluoro-4-nitrophenoxy)pyridin-3-yl)prop-2-ynyl)azetidin-3-yl)methylcarbamate (30 mg, 0.66 mmol) in the same manner as in Step E of Example 35 using Fe powder (50 mg, 0.091 mmol) and NH4Cl (96 mg, 1.82 mmol). The product was used in subsequent re... | CC(C)(C)OC(=O)NCC1CN(CC#Cc2cnccc2Oc2ccc(N)cc2F)C1 | null | null | null |
1,326,064 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [CH3:1][C@@H:2]([OH:6])[C@H:3]([OH:5])[CH3:4].[H-].[Na+].[Br:9][C:10]1[C:11](Cl)=[N:12][C:13]([Cl:16])=[N:14][CH:15]=1>C1COCC1>[Br:9][C:10]1[C:11]([O:5][C@H:3]([CH3:4])[C@H:2]([OH:6])[CH3:1])=[N:12][C:13]([Cl:16])=[N:14][CH:15]=1 | C[C@@H](O)[C@@H](C)O | Clc1ncc(Br)c(Cl)n1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 0.17 | A solution of 1.35 g (15.0 mmol) of (R,R)-(−)-2,3-butanediol in 50 ml of THF is mixed at 0° C. in portions with 480 mg (11.0 mmol) of sodium hydride (55% dispersion) and then stirred for 10 minutes at room temperature. The solution that is produced is added at 0° C. to 2.27 g (10.0 mmol) of 5-bromo-2,4-dichloropyrimidi... | C[C@@H](O)[C@@H](C)Oc1nc(Cl)ncc1Br | null | null | null |
403,523 | ord_dataset-55e306db9b6b4befbc22504c12b7113d | null | 1998-01-01T00:06:00 | true | [CH:1]1[C:6]([NH:7][NH2:8])=[CH:5][CH:4]=[C:3]([S:9]([NH2:12])(=[O:11])=[O:10])[CH:2]=1.Cl.[CH3:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[C:21](=O)[CH:20]([C:26](=O)[C:27]([F:30])([F:29])[F:28])[CH2:19][CH2:18]2>C(O)C>[CH3:14][C:15]1[CH:24]=[CH:23][C:22]2[C:21]3[N:7]([C:6]4[CH:1]=[CH:2][C:3]([S:9]([NH2:12])(=[... | NNc1ccc(S(N)(=O)=O)cc1 | Cc1ccc2c(c1)CCC(C(=O)C(F)(F)F)C2=O | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | 14.8 | 4-Sulfonamidophenylhydrazine hydrochloride (1.80 g, 8.0 mmol) was added to a stirred solution of the diketone from Step 1 (1.86 g, 7.3 mmol) in ethanol (10 mL). The reaction was heated to reflux and stirred for 14.8 hours. The reaction mixture was cooled and filtered. The filtrate was concentrated in vacuo, dissolved i... | Cc1ccc2c(c1)CCc1c(C(F)(F)F)nn(-c3ccc(S(N)(=O)=O)cc3)c1-2 | null | 63.9 | null |
889,923 | ord_dataset-11068b1e475b4c5b82e56726ab0dddb7 | null | 2009-01-01T00:07:00 | true | [CH3:1][C:2]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[S:4][CH:3]=1.[Li]CCCC.CCCCCC.[CH2:22]([CH:24]([C:27]1[C:28]2[N:29]([C:34](I)=[C:35]([CH3:37])[N:36]=2)[N:30]=[C:31]([CH3:33])[CH:32]=1)[CH2:25][CH3:26])[CH3:23]>C1COCC1.[Cl-].[Cl-].[Zn+2]>[CH2:22]([CH:24]([C:27]1[C:28]2[N:29]([C:34]([C:3]3[S:4][C:5]4=[CH:6][N:7]=[C... | Cc1csc2cnccc12 | CCC(CC)c1cc(C)nn2c(I)c(C)nc12 | null | [Cl-] | [Li]CCCC | [Zn+2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCCC | C1CCOC1 | null | null | null | null | null | null | null | null | null | -78 | 0.17 | 149 mg of 3-Methyl-thieno[2,3-c]pyridine (1.0 mmol) is dissolved in 3.0 ml of dry THF and cooled to −78° C. 0.48 ml of n-BuLi 2.5M in hexane (1.2 mmol) is added at −78° C. and stirred at −78° C. for 10 min and room temperature for 10 min. The reaction vessel is cooled to −78° C. again and 2.6 ml of 0.5M ZnCl2 in THF (1... | CCC(CC)c1cc(C)nn2c(-c3sc4cnccc4c3C)c(C)nc12 | null | 44.9 | null |
1,322,525 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | Cl.Cl.[NH2:3][C@H:4]1[CH:9]2[CH2:10][CH2:11][N:6]([CH2:7][CH2:8]2)[CH2:5]1.O=[CH:13][CH2:14][C:15]1[C:23]2[C:22]([C:24]([O:26][CH3:27])=[O:25])=[CH:21][CH:20]=[CH:19][C:18]=2[N:17]([S:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)(=[O:30])=[O:29])[CH:16]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C.ClCCl>[C:31... | COC(=O)c1cccc2c1c(CC=O)cn2S(=O)(=O)c1ccccc1 | N[C@@H]1CN2CCC1CC2 | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | Cl | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 16 | A mixture of (S)-(−)-3-aminoquinuclidine dihydrochloride (202 mg, 1.01 mmol) and methyl 3-(2-oxoethyl)-1-(phenylsulfonyl)-1H-indole-4-carboxylate (330 mg, 0.92 mmol) from Step C above in 1% acetic acid in dichloromethane (20 mL) was stirred at ambient temperature for 16 h. Sodium triacetoxyborohydride (584 mg, 2.76 mmo... | COC(=O)c1cccc2c1c(CCN[C@@H]1CN3CCC1CC3)cn2S(=O)(=O)c1ccccc1 | null | 40 | null |
1,444,966 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [N:1]1([S:7]([CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([C@@H:18]3[CH2:22][CH2:21][C:20](=[O:23])[CH2:19]3)=[CH:14][CH:13]=2)(=[O:9])=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1>CCOC(C)=O.[Pd]>[N:1]1([S:7]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C@@H:18]3[CH2:22][CH2:21][C:20](=[O:23])[CH2:19]3)=[CH:14][CH:13]=2)(=... | O=C1CC[C@@H](c2ccc(C=CS(=O)(=O)N3CCOCC3)cc2)C1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | A solution of (3R)-3-{4-[2-(morpholine-4-sulfonyl)-vinyl]-phenyl}-cyclopentanone (210 mg) in EtOAc (10 ml) containing Pd/C (10%, 50 mg) was hydrogenated over night at r.t. The mixture is filtered and solvents are removed in vacuo to afford the 1H NMR (300 MHz, CDCl3) δ 7.25-7.17 (m, 4H), 3.75 (m, 4H), 3.48-3.34 (m, 1H)... | O=C1CC[C@@H](c2ccc(CCS(=O)(=O)N3CCOCC3)cc2)C1 | null | null | null |
479,073 | ord_dataset-21c1b1c06c7e4e09a38b5b1c71a32e52 | null | 2000-01-01T00:10:00 | true | [F:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([F:11])[CH:10]=1)[NH:7][CH:6]=[C:5]2[C:12]1[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH:17]=1.[C:19]1([S:25](Cl)(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([F:11])[CH:10]=1)[N:7]([S:25]([C:19]1... | O=S(=O)(Cl)c1ccccc1 | CN1CC=C(c2c[nH]c3c(F)cc(F)cc23)CC1 | null | C[Si](C)(C)[N-][Si](C)(C)C | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | (8.5 mg, 54%); from 5,7-difluoro-3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (Example 4g, 10 mg, 0.04 mmol) and phenylsulfonylchloride (10.6 mg, 0.06 mmoles) with 1M NaN(TMS)2 (60 μL, 0.06mmol) in THF (0.5 mL) at RT. | CN1CC=C(c2cn(S(=O)(=O)c3ccccc3)c3c(F)cc(F)cc23)CC1 | null | null | null |
1,448,040 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][CH3:11])=[N:8][CH:9]=1)(=[O:3])[CH3:2].[F:12][C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([F:21])[CH:20]=1)[CH:16]=O.[OH-].[K+]>>[F:12][C:13]1[CH:14]=[C:15](/[CH:16]=[CH:2]/[C:1]([C:4]2[CH:9]=[N:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=2)=[O:3])[CH:18]=[C:19]([F:21])[CH:20]=1 | COc1ccc(C(C)=O)cn1 | O=Cc1cc(F)cc(F)c1 | null | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In analogy to example 170, step 1, 5-acetyl-2-methoxypyridine was reacted with 3,5-difluorobenzaldehyde in the presence of potassium hydroxide to give the title compound as a colourless solid. MS (ESI+): m/z=276.2 [M+H]+. | COc1ccc(C(=O)/C=C/c2cc(F)cc(F)c2)cn1 | null | null | null |
691,696 | ord_dataset-6214af00a7eb47f3887ef21a94320a7e | null | 2005-01-01T00:11:00 | true | [NH2:1][C:2]1[C:11]([C:12]#[N:13])=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O>[NH2:1][C:2]1[C:11]([C:12]#[N:13])=[C:10]([NH:22][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1 | N#Cc1c(N)nc2ccccc2c1Cl | NCc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 130 | null | 5 g of 2-amino-3-cyano4-chloroquinoline and 11 ml of benzylamine are heated under stirring at 130° C. The reaction mixture is poured onto 50 ml of water, the resulting precipitate is filtered off, washed with 50 ml of water. The pale-yellow precipitate is recrystallized from dimethylformamide to obtain 5.2 g of the tit... | N#Cc1c(N)nc2ccccc2c1NCc1ccccc1 | null | null | null |
1,155,383 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | [C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([F:17])=[CH:14][CH:15]=2)[C:10]([CH3:18])=[C:9]1[S:19](=[O:33])(=[O:32])[NH:20][C:21]1[CH:26]=[CH:25][C:24](Br)=[CH:23][C:22]=1[C:28]([F:31])([F:30])[F:29])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=1>COCCOC.C(O)C.C(=O)([O-])[O... | Cc1c(S(=O)(=O)Nc2ccc(Br)cc2C(F)(F)F)n(C(=O)OC(C)(C)C)c2ccc(F)cc12 | OB(O)c1ccncc1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCOC | CCO | null | null | null | null | null | null | null | null | null | null | null | This compound was prepared in analogy to Example 2 starting from 2-(4-bromo-2-trifluoromethyl-phenylsulfamoyl)-5-fluoro-3-methyl-indole-1-carboxylic acid tert-butyl ester (0.108 g), 4-pyridineboronic acid (0.036 g) in 1,2-dimethoxyethane (5.0 ml), ethanol (0.4 ml) and 2 M aqueous sodium carbonate solution (0.8 ml) with... | Cc1c(S(=O)(=O)Nc2ccc(-c3ccncc3)cc2C(F)(F)F)n(C(=O)OC(C)(C)C)c2ccc(F)cc12 | null | 53.9 | null |
1,118,028 | ord_dataset-4226e9b4f9f845db967ed997270dcafc | null | 2011-01-01T00:12:00 | true | [OH:1][CH:2]1[CH2:11][CH2:10][NH:9][C:8]2[N:7]=[CH:6][C:5]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([N:20]4[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]4)=[O:19])=[CH:14][CH:13]=3)=[CH:4][C:3]1=2.[F:27][C:28]1[CH:33]=[CH:32][C:31]([C:34](=[O:36])[CH3:35])=[C:30](O)[CH:29]=1>CO.C(Cl)Cl>[F:27][C:28]1[CH:33]=[CH:32][C:31]([... | CC(=O)c1ccc(F)cc1O | CN1CCN(C(=O)c2ccc(-c3cnc4c(c3)C(O)CCN4)cc2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CO | null | null | null | null | null | null | null | null | null | null | null | [4-(5-Hydroxy-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)phenyl]-(4-methylpiperazin-1-yl)methanone (30 mg) was reacted with 1-(4-fluoro-2-hydroxyphenyl)ethanone (39.4 mg) as in General Procedure 12. Silica gel chromatography using a gradient of 0-15% methanol/CH2Cl2 as the eluting solvent gave the title compound as a ye... | CC(=O)c1ccc(F)cc1OC1CCNc2ncc(-c3ccc(C(=O)N4CCN(C)CC4)cc3)cc21 | null | 53 | null |
1,102,531 | ord_dataset-375a420ee9b042918ddca20f02df37d3 | null | 2011-01-01T00:11:00 | true | [CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[CH:14]=[C:13]([C:15]([O:17]CC)=[O:16])[N:12]([CH2:20][CH2:21][O:22][CH:23]3[CH2:28][CH2:27][CH2:26][CH:25]([O:29][CH2:30][C:31]4[N:32]=[C:33]([C:37]5[CH:38]=[C:39]([CH3:43])[CH:40]=[CH:41][CH:42]=5)[O:34][C:35]=4[CH3:36])[CH2:24]3)[C:9]2=[CH:10][N:11]=1>C1COCC1.CO.[OH-... | CCOC(=O)c1cc2cc(OCCOC)ncc2n1CCOC1CCCC(OCc2nc(-c3cccc(C)c3)oc2C)C1 | null | null | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 24 | 60 mg of ethyl 5-(2-methoxyethoxy)-1-{2-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy]ethyl}-1H-pyrrolo[2,3-c]pyridine-2-carboxylate are dissolved in 2 ml of THF/methanol 3:1, and 0.15 ml of a 1 N lithium hydroxide solution is added. The mixture is stirred at room temperature for 24 h. All volatile components ... | COCCOc1cc2cc(C(=O)O)n(CCO[C@@H]3CCC[C@H](OCc4nc(-c5cccc(C)c5)oc4C)C3)c2cn1 | null | null | null |
745,919 | ord_dataset-4b705442211b4a3988e26d5f65098160 | null | 2006-01-01T00:12:00 | true | C[O:2][C:3]([C:5]1[N:6]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([O:28]C)=[O:27])[CH:21]=2)[C:7]2[C:12]([C:13]=1[CH2:14][CH2:15][S:16]C(=O)C)=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4].[OH-].[K+].Cl>C1COCC1>[C:26]([C:22]1[CH:21]=[C:20]([N:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:13]([CH2:14][CH2:15][SH:16])=[C:5]... | COC(=O)c1cccc(-n2c(C(=O)OC)c(CCSC(C)=O)c3ccccc32)c1 | null | null | Cl | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 8 | To a solution of 3-(2-acetylsulfanyl-ethyl)-1-(3-methoxycarbonyl-phenyl)-1H-indole-2-carboxylic acid methyl ester (0.32 g, 0.73 mmol) in THF (10 mL) was dropwise added 0.5 N KOH (10 mL) and the resulting mixture was stirred at room temperature overnight. The reaction acidified with 3 N HCl and the resulting white preci... | O=C(O)c1cccc(-n2c(C(=O)O)c(CCS)c3ccccc32)c1 | null | 88.3 | null |
793,294 | ord_dataset-744b04e8228742eb9aa4bde36f5dedf1 | null | 2007-01-01T00:10:00 | true | Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][N:13]=2)=[CH:7][CH:6]=1)=[O:3].[CH3:22][N:23]([CH3:43])[C:24]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:25]=1[CH:26]=[CH:27][CH:28]=[C:29]2[S:34]([N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1)(=[O:36])=[O:35]>>[F:19... | O=C(Cl)Oc1ccc(Oc2ccc(C(F)(F)F)cn2)cc1 | CN(C)c1cccc2c(S(=O)(=O)N3CCNCC3)cccc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from 4-(5-trifluoromethyl-pyridin-2-yloxy)-phenyl chloroformate and 1-(5-dimethylamino-naphthalene-1-sulfonyl)-piperazine and purified by flash chromatography (ethyl acetate—heptane 1:4), yield 32%. Pale crystals, HPLC-MS: m/z: 601(M+1) at Rt=5.2 min.; m.p. ° C.; IR (KBr): ν 1723 (C═O) c... | CN(C)c1cccc2c(S(=O)(=O)N3CCN(C(=O)Oc4ccc(Oc5ccc(C(F)(F)F)cn5)cc4)CC3)cccc12 | null | 32 | null |
1,423,207 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | [C:1]([Si:5]([CH3:21])([CH3:20])[O:6][CH:7]1[CH2:12][CH2:11][C:10](=[N:13][S:14]([C:16]([CH3:19])([CH3:18])[CH3:17])=[O:15])[CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[CH:22]1([Mg]Br)[CH2:24][CH2:23]1>C(OCC)C>[C:1]([Si:5]([CH3:21])([CH3:20])[O:6][CH:7]1[CH2:8][CH2:9][C:10]([NH:13][S:14]([C:16]([CH3:19])([CH3:18])[CH3:17... | Br[Mg]C1CC1 | CC(C)(C)S(=O)N=C1CCC(O[Si](C)(C)C(C)(C)C)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | -78 | 1 | A solution of 3.00 g (9.05 mmol) of 2-methyl-propane-2-sulfinic acid [4-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-amide (25) in 15 mL of diethyl ether was added dropwise to 54.3 mL (27.1 mmol) of a 0.5 M solution of cyclopropylmagnesium bromide in diethyl ether precooled to −78° C. The reaction solution was sti... | CC(C)(C)S(=O)NC1(C2CC2)CCC(O[Si](C)(C)C(C)(C)C)CC1 | null | null | null |
21,228 | ord_dataset-39f318aa6ec5450182abaf3662294306 | null | 1977-01-01T00:03:00 | true | [S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:36](=[O:37])[N:12]2[CH:13]([C:20]([O:22][CH:23]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])[C:14]([CH:17]([OH:19])[CH3:18])=[CH:15][S:16][C@H:11]12)=[O:8].N1C=CC=CC=1.[C:44](OC(=O)C)(=[O:46])[CH3:45]... | CC(=O)OC(C)=O | CC(O)C1=CS[C@@H]2C(NC(=O)Cc3cccs3)C(=O)N2C1C(=O)OC(c1ccccc1)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | A solution of 0.535 g. of benzhydryl 7-(2-thienylacetamido)-3-(1-hydroxyethyl)-2-cephem-4-carboxylate, 6 ml. of pyridine, and 2 ml. of acetic anhydride in 30 ml. of methylene chloride was refluxed at 42° C. for 2 hours. The reaction mixture was then evaporated in vacuo to dryness, and the resulting residue was dissolve... | CC(=O)OC(C)C1=CS[C@@H]2C(NC(=O)Cc3cccs3)C(=O)N2C1C(=O)OC(c1ccccc1)c1ccccc1 | null | 99 | null |
1,603,726 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[N:7]=[C:6]2O.O=P(Cl)(Cl)[Cl:22]>CN(C)C1C=CC=CC=1>[Cl:22][C:6]1[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[C:8]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[N:7]=1 | O=P(Cl)(Cl)Cl | COc1ccc2nc(-c3cccnc3)nc(O)c2c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | 120 | 0.5 | To a mixture of 6-methoxy-2-(pyridin-3-yl) quinazolin-4-ol (600 mg, 2.37 mmol) in POCl3 (5 mL) was added N,N-dimethyl aniline (1 drop). The resulting mixture was stirred at 120° C. for 30 min. After the reaction was completed, POCl3 was removed in vacuo, and the residue was added to ice-water slowly. The pH was adjuste... | COc1ccc2nc(-c3cccnc3)nc(Cl)c2c1 | null | 40.4 | null |
806,007 | ord_dataset-ed846b4b229e4bb09ad9dba95ad7ebeb | null | 2008-01-01T00:01:00 | true | [C:1]1(=[O:8])[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.[Li][CH2:10][CH2:11][CH2:12][CH3:13]>CCOCC>[CH2:10]([C:1]1([OH:8])[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1)[CH2:11][CH2:12][CH3:13] | [Li]CCCC | O=C1C=CCCCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | 0 | 2 | To a clear solution of 2-cyclohepten-1-one (5 g, 45.5 mmol) in ether (50 mL), cooled to 0° C., was added n-BuLi (2.0 M in hexanes, 25 mL, 50.0 mmol) dropwise to produce an opaque yellow solution. The reaction stirred for 2 h at 0° C. and then warmed to room temperature. After 1 h, the reaction was complete as determine... | CCCCC1(O)C=CCCCC1 | null | 26.1 | null |
141,702 | ord_dataset-84dc0c9e5fb4424687194ef8d14d1c22 | null | 1986-01-01T00:04:00 | true | Br[C@@H:2](C)[C:3](OC)(OC)[C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:14][CH3:15])[CH:10]=2)[CH:5]=1.[C:21]([O-:24])(=[O:23])C.[K+].CN(C)C=O>O>[CH3:15][O:14][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[CH:5]=[C:4]([C@H:3]([CH3:2])[C:21]([OH:24])=[O:23])[CH:13]=[CH:12]2 | COc1ccc2cc(C(OC)(OC)[C@H](C)Br)ccc2c1 | CC(=O)[O-] | null | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | A mixture of (+)(S)2-bromo-1,1-dimethoxy-1-(6-methoxy-2-naphthyl)-propane (3.39 g; 10 mmol), potassium acetate (1.2 g; 12 mmol), N,N-dimethylformamide (14 ml) and of water (8 ml) is heated at 100° C. under stirring. The reaction mixture is worked up as described in example 1 to provide (+)(S)2-(6-methoxy-2-naphthyl)-pr... | COc1ccc2cc([C@H](C)C(=O)O)ccc2c1 | null | 97 | null |
396,991 | ord_dataset-a4a191e812a64d0598ea918f047e8da7 | null | 1998-01-01T00:04:00 | true | C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[C:32]([O:36][C:37]([N:39]1[CH2:44][CH2:43][N:42]([C:45]([C:47]2[C:56]3[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=3)[CH:50]=[CH:49][CH:48]=2)=[O:46])[CH2:41][C@@H:40]1[CH2:57][CH2:58]O)=[O:38])([CH3:35])([CH3:34])[CH3:33].[S:60]1C=C[CH:62]=[C:61]1CC(O)=O>O1CCCC1>[... | O=C(O)Cc1cccs1 | CC(C)(C)OC(=O)N1CCN(C(=O)c2cccc3ccccc23)C[C@@H]1CCO | null | CCOC(=O)/N=N/C(=O)OCC | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 0.5 | Triphenylphosphine (0.65 g, 2.5 mmol), in tetrahydrofuran (7 mL) was cooled to 0° C. and diethylazodicarboxylate (0.41 mL, 2.5 mmol) added. The reaction was stirred for 30 min, and 1-tert-butoxycarbonyl-2(S)-(2-hydroxyethyl)-4-naphthoylpiperazine (0.50 g, 1.3 mmol) and thiolacetic acid (0.18 mL, 2.5 mmol) were added in... | CC(=S)CC[C@H]1CN(C(=O)c2cccc3ccccc23)CCN1C(=O)OC(C)(C)C | null | null | null |
404,191 | ord_dataset-55e306db9b6b4befbc22504c12b7113d | null | 1998-01-01T00:06:00 | true | [NH2:1][CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])[C:6]2[CH:16]=[CH:17][CH:18]=[CH:19][C:5]=2[N:4]([CH2:20][C:21]([N:23]2[CH2:28][CH2:27][S:26][CH2:25][CH2:24]2)=[O:22])[C:3]1=[O:29].[CH3:30][C:31]1[CH:32]=[C:33]([N:37]=[C:38]=[O:39])[CH:34]=[CH:35][CH:36]=1>C(Cl)Cl>[F:15][C:10]1[CH:11]=[CH:1... | NC1N=C(c2ccccc2F)c2ccccc2N(CC(=O)N2CCSCC2)C1=O | Cc1cccc(N=C=O)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | 8 | To a solution of (3RS)-3-amino-2,3-dihydro-5-(2-fluorophenyl)-1-(thiomorpholin-4-yl)carbonylmethyl-1H-1,4-benzodiazepin-2-one (0.11 g) in dry methylene chloride (10 ml) was added dropwise a solution of 3-methylphenyl isocyanate (0.043 g) in dry methylene chloride (5 ml) at ambient temperature. After completion of addit... | Cc1cccc(NC(=O)NC2N=C(c3ccccc3F)c3ccccc3N(CC(=O)N3CCSCC3)C2=O)c1 | null | 68.7 | null |
399,582 | ord_dataset-7fed188163cf4ccca934ec71504c7f8a | null | 1998-01-01T00:05:00 | true | C(OC([NH:11][C@@H:12]([C:22]1[NH:26][N:25]=[N:24][N:23]=1)[CH2:13][CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=O)C1C=CC=CC=1>C(O)C.[Pd]>[NH2:11][C@@H:12]([C:22]1[NH:26][N:25]=[N:24][N:23]=1)[CH2:13][CH2:14][C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16] | CC(C)(C)OC(=O)CC[C@@H](NC(=O)OCc1ccccc1)c1nnn[nH]1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | A solution of tert-butyl (4R)-4-(benzyloxycarbonylamino)-4-(tetrazol-5-yl)-butyrate (1.2 g, 3.32 mmol) in ethanol (77 ml) was stirred with 10% Pd-C (0.166 g) under a hydrogen atmosphere at ambient temperature for 16 hours. The catalyst was removed by filtration and the filtrate evaporated. Dichloromethane was added to ... | CC(C)(C)OC(=O)CC[C@@H](N)c1nnn[nH]1 | null | 91.1 | null |
1,360,610 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | [F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:3]=1[F:15].C([Li])(CC)C.[O:21]1[C:25]2([CH2:30][CH2:29][C:28](=O)[CH2:27][CH2:26]2)[O:24][CH2:23][CH2:22]1.[Cl-].[NH4+]>C(OCC)(=O)C.C1COCC1>[F:1][C:2]1[C:3]([F:15])=[C:4]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH... | O=C1CCC2(CC1)OCCO2 | CCCCCCOc1cccc(F)c1F | null | [Cl-] | [Li]C(C)CC | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 30 | 2 | 1,2-Difluoro-3-hexyloxybenzene (s-1) (100.0 g) and THF (1,000 ml) were placed in a reaction vessel under an atmosphere of nitrogen, and cooled to −74° C. sec-Butyllithium (1.00M; n-hexane and cyclohexane solution; 357 ml) was added dropwise in the temperature range of −74° C. to −70° C., and the stirring was continued ... | CCCCCCOc1ccc(C2CCC3(CC2)OCCO3)c(F)c1F | null | 87.3 | null |
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