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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1,439,988 | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | null | 2014-01-01T00:06:00 | true | [OH:1][C:2]1[C:7]2[C@@:8]3([OH:45])[C@@:21]([O:25][CH3:26])([C@H:22]([OH:24])[CH2:23][C:6]=2[CH:5]=[C:4]([CH3:46])[C:3]=1[C:47](O)=[O:48])[C:20](=[O:27])[C:19]1[C:10](=[CH:11][C:12]2[C:13](=[O:43])[C:14]([NH:30][CH:31]4[C@H:36]([O:37][CH3:38])[C@H:35]([OH:39])[C@@H:34]([O:40][CH3:41])[C@H:33]([CH3:42])[O:32]4)=[CH:15][... | CO[C@@H]1[C@@H](O)[C@@H](OC)C(NC2=CC(=O)c3c(cc4c(c3O)C(=O)[C@]3(OC)[C@H](O)Cc5cc(C)c(C(=O)O)c(O)c5[C@]3(O)C4=O)C2=O)O[C@H]1C | Nc1cccnc1 | null | On1nnc2ccccc21 | null | 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 | 25 | 12 | To a solution of (6R,6aS,14aR)-1,6,8,14a-tetrahydroxy-11-((3R,4R,5R,6S)-4-hydroxy-3,5-dimethoxy-6-methyltetrahydro-2H-pyran-2-ylamino)-6a-methoxy-3-methyl-7,9,12,14-tetraoxo-5,6,6a,7,9,12,14,14a-octahydrobenzo[a]tetracene-2-carboxylic acid (50 mg, 0.073 mmol) in THF (5 mL) were added 3-aminopyridine (14 mg, 0.15 mmol),... | CO[C@@H]1[C@@H](O)[C@@H](OC)C(NC2=CC(=O)c3c(cc4c(c3O)C(=O)[C@]3(OC)[C@H](O)Cc5cc(C)c(C(=O)Nc6cccnc6)c(O)c5[C@]3(O)C4=O)C2=O)O[C@H]1C | null | 9 | null |
382,342 | ord_dataset-f367d8d2baac490b9204609a79420961 | null | 1997-01-01T00:11:00 | true | B.O1CCCC1.[CH2:7]([O:11][C:12]1[C:17]([C:18]#[N:19])=[CH:16][C:15]([C:20]2[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][CH:21]=2)=[C:14]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[N:13]=1)[CH2:8][CH2:9][CH3:10].CO>O1CCCC1>[CH2:7]([O:11][C:12]1[C:17]([CH2:18][NH2:19])=[CH:16][C:15]([C:20]2[... | CCCCOc1nc(-c2ccc(F)cc2)c(-c2ccc(S(C)(=O)=O)cc2)cc1C#N | null | null | B | null | 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 | 1 | Borane-tetrahydrofuran (1.0M in tetrahydrofuran, 1.5 mL, 0.0016 mole) was added by syringe to a solution of 2-butoxy-6-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]pyridine-3-carbonitrile (Example 14) (0.68 g, 0.0016 mole) in tetrahydrofuran (100 mL). After stirring at room temperature for 1 hour the solution was heate... | CCCCOc1nc(-c2ccc(F)cc2)c(-c2ccc(S(C)(=O)=O)cc2)cc1CN | null | null | null |
349,970 | ord_dataset-66f304805e5d47fc8d3c722b1bd8dfa2 | null | 1996-01-01T00:12:00 | true | [C:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9](Cl)=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[N+]([O-])(O)=O.[N+:18]([O:21][CH2:22][CH2:23][NH2:24])([O-:20])=[O:19]>>[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH:24][CH2:23][CH2:22][O:21][N+:18]([O-:20])=[O:19])=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2] | CC(=O)Oc1ccc(C(=O)Cl)cc1 | NCCO[N+](=O)[O-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=[N+]([O-])O | null | null | null | null | null | null | null | null | null | null | null | null | Starting from 0.113 mole of 4-acetoxybenzoic acid chloride and 0.110 mole of 2-nitrooxy-ethylamine nitrate, and operating substantially as described in the preceding Example, 22 g of the title compound were obtained. M.p. 95°-97° C. (ethyl ether). | CC(=O)Oc1ccc(C(=O)NCCO[N+](=O)[O-])cc1 | null | 74.6 | null |
1,141,098 | ord_dataset-68715347640045adb1b09e6a04722b0e | null | 2012-01-01T00:03:00 | true | O.[NH2:2][NH2:3].C[O:5][C:6](=O)[C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1>CO>[NH:2]([C:6]([C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1)=[O:5])[NH2:3] | NN | COC(=O)c1ccc(C(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CO | null | null | null | null | null | null | null | null | null | null | 1 | Hydrazine hydrate was added to a solution of terephthalic acid monomethyl ester (1 g, 5.5 mmol) in MeOH (10 mL) and stirring was continued for 1 hr. The reaction mixture was concentrated to afford 900 mg (90.09% Yield) of 4-hydrazinocarbonyl-benzoic acid. p-Toluene sulfonic acid (48 mg, 0.277 mmol) was added to a solut... | NNC(=O)c1ccc(C(=O)O)cc1 | null | 90.09 | null |
1,031,244 | ord_dataset-83acb82dc5ba4f7aba439b9875aaac43 | null | 2011-01-01T00:02:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:22])[C:10]2[CH:15]=[CH:14][C:13]([CH2:16][S:17]([CH3:20])(=[O:19])=[O:18])=[C:12]([OH:21])[CH:11]=2)=[CH:4][C:3]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1.Br[CH2:30][CH:31]([CH3:33])[CH3:32]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:22])[C:10]2[CH:15]=[CH:14][C:... | CC(C)CBr | CS(=O)(=O)Cc1ccc(C(=O)Nc2ccc(Cl)c(-c3ccccn3)c2)cc1O | 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 | N-(4-chloro-3-(pyridin-2-yl)phenyl)-3-hydroxy-4-(methylsulfonylmethyl)benzamide (50 mg, 0.12 mmol) was treated with 1-bromo-2-methylpropane (26 μl, 0.24 mmol) via procedure U to yield 19 mg of N-(4-chloro-3-(pyridin-2-yl)phenyl)-3-isobutoxy-4-(methylsulfonylmethyl)benzamide. MS (Q1) 473 (M)+. | CC(C)COc1cc(C(=O)Nc2ccc(Cl)c(-c3ccccn3)c2)ccc1CS(C)(=O)=O | null | 33.5 | null |
1,754,137 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [CH:1]1([C:4]2[C:5]([O:13][CH2:14][C:15]([F:18])([F:17])[F:16])=[CH:6][C:7]([C:10]([OH:12])=O)=[N:8][CH:9]=2)[CH2:3][CH2:2]1.[CH3:19][C:20]([CH3:30])([CH3:29])[CH:21]([C:23]1[O:24][C:25]([CH3:28])=[N:26][N:27]=1)[NH2:22]>>[CH:1]1([C:4]2[C:5]([O:13][CH2:14][C:15]([F:18])([F:17])[F:16])=[CH:6][C:7]([C:10]([NH:22][CH:21](... | Cc1nnc(C(N)C(C)(C)C)o1 | O=C(O)c1cc(OCC(F)(F)F)c(C2CC2)cn1 | 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 synthesized in analogy to Example 112e, using 5-Cyclopropyl-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid (Example 48c) and 2,2-dimethyl-1-(5-methyl-1,3,4-oxadiazol-2-yl)propan-1-amine (example 174b) as starting materials and isolated (128 mg, 81%); MS (ESI, m/z): 413.6 (M+H+). | Cc1nnc(C(NC(=O)c2cc(OCC(F)(F)F)c(C3CC3)cn2)C(C)(C)C)o1 | null | null | null |
107,492 | ord_dataset-29d79fca4cec4a43b773d0ba25b27651 | null | 1983-01-01T00:08:00 | true | Cl.[C:2](Cl)([CH3:5])([CH3:4])[CH3:3].[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>>[C:2]([C:11]1[CH:12]=[CH:13][C:8]([Cl:7])=[CH:9][CH:10]=1)([CH3:5])([CH3:4])[CH3:3] | Clc1ccccc1 | CC(C)(C)Cl | 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 | 30 | null | To 16.9 g of chlorobenzene was added 1.5 g of ferric chloride, and hydrogen chloride gas was blown into the mixture for minutes. Then, 46 g of tert-butyl chloride was added dropwise to the mixture at 30° C. over a period of 1 hour. The mixture was maintained at 30° C. for 2 hours. The reaction mixture was washed with a... | CC(C)(C)c1ccc(Cl)cc1 | null | 98.7 | null |
271,899 | ord_dataset-347c0709d28a44dea43ca42052be4db3 | null | 1993-01-01T00:07:00 | true | [C:1]1([CH2:9][NH2:10])[CH:6]=[CH:5][C:4]([CH2:7][NH2:8])=[CH:3][CH:2]=1.CCCCCC.[C:17]([N:21]=[C:22]=[O:23])([CH3:20])([CH3:19])[CH3:18]>C(Cl)Cl>[C:17]([NH:21][C:22](=[O:23])[NH:8][CH2:7][C:4]1[CH:5]=[CH:6][C:1]([CH2:9][NH2:10])=[CH:2][CH:3]=1)([CH3:20])([CH3:19])[CH3:18] | NCc1ccc(CN)cc1 | CC(C)(C)N=C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCCCCC | null | null | null | null | null | null | null | null | null | null | 2 | To a solution of 2.7 g p-xylylenediamine in 100 ml methylene dichloride, was added slowly with stirring 10 ml of a n-hexan solution containing 990 mg t-butyl isocyanate under ice cooling. Stirring was continued at room temperature for two hours, the solvent was distilled off under reduced pressure, and the residue was ... | CC(C)(C)NC(=O)NCc1ccc(CN)cc1 | null | 42.6 | null |
1,738,830 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | [CH2:1]([N:8]1[CH2:13][C:12]([F:15])([F:14])[C:11]([OH:16])=[C:10](C(OCC)=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[O:23]1CCOCC1>>[CH2:1]([N:8]1[CH2:9][CH2:10][C:11]([OH:16])([OH:23])[C:12]([F:14])([F:15])[CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1 | CCOC(=O)C1=C(O)C(F)(F)CN(Cc2ccccc2)C1 | C1COCCO1 | 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 | 80 | 3 | A mixture of ethyl 1-benzyl-5,5-difluoro-4-hydroxy-1,2,5,6-tetrahydropyridine-3-carboxylate (5.0 g) and conc. hydrochloric acid (40 mL) in 1,4-dioxane (15 mL) was stirred at 80° C. for 3 hr. The reaction mixture was concentrated under reduced pressure, and diluted with ethyl acetate, and the mixture was adjusted to pH-... | OC1(O)CCN(Cc2ccccc2)CC1(F)F | null | null | null |
1,528,948 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [CH3:1][N:2]1[C:7](=[O:8])[C:6]([NH:9][C:10]2[CH:19]=[C:13]3[CH2:14][N:15]([CH3:18])[CH2:16][CH2:17][N:12]3[N:11]=2)=[CH:5][C:4]([C:20]2[CH:25]=[CH:24][N:23]=[C:22]([N:26]3[C:38](=[O:39])[C:37]4[N:29]([C:30]5[C@@H:31]6[CH2:40][C@H:34]([C:35]=5[CH:36]=4)[CH2:33][CH2:32]6)[CH2:28][CH2:27]3)[C:21]=2[CH:41]=[O:42])=[CH:3]1... | CN1CCn2nc(Nc3cc(-c4ccnc(N5CCn6c(cc7c6[C@H]6CC[C@@H]7C6)C5=O)c4C=O)cn(C)c3=O)cc2C1 | null | null | [BH4-] | [Na+] | 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 | 20 | 2 | A solution of 167h (120 mg, 0.21 mmol) in methanol (20 mL) was added NaBH4 (24 mg, 0.63 mmol). The mixture was stirred at 20° C. for 2 h. The reaction was quenched with water and concentrated under reduced pressure. The residue was purified by reverse-phase prep-HPLC to afford 167 (98 mg, 83%) as a yellow solid. MS-ESI... | CN1CCn2nc(Nc3cc(-c4ccnc(N5CCn6c(cc7c6C6CCC7C6)C5=O)c4CO)cn(C)c3=O)cc2C1 | null | 82.4 | null |
36,696 | ord_dataset-3e699bae9dce4a0f996c34a7c5a4b79a | null | 1978-01-01T00:02:00 | true | [C:1]([CH2:4][C:5](=[O:7])[CH3:6])(=[O:3])[CH3:2].N.[CH2:9](Br)[CH:10]=[CH2:11].[Cl-].[NH4+]>>[CH3:6][C:5](=[O:7])[CH2:4][C:1](=[O:3])[CH2:2][CH2:11][CH:10]=[CH2:9] | CC(=O)CC(C)=O | C=CCBr | null | N | [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 | 0.5 | After 30 minutes, a powdery complex compound produced by mixing acetylacetone (15 g; 10.15 mol) with ammonia was gradually added to the solution. The mixture was stirred for about 1 hour, and then allyl bromide (18.2 g; 0.15 mol) was added to it. After stirring 1 hour, the solution was neutralized with solid ammonium c... | C=CCCC(=O)CC(C)=O | null | 48 | null |
785,492 | ord_dataset-4ad5db8537994579bef51f16dd8bf0bd | null | 2007-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([CH:14]2[CH2:16][CH2:15]2)=[O:13])=[C:7]2[C:3]=1[CH2:4][N:5]([C@@H:18]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH2:32][CH3:33])[CH:24]=1)[CH2:19][C:20](O)=[O:21])[C:6]2=[O:17].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[NH2:47][OH:48].O>O1CCCC1>[Cl:1][C:2]1[CH:10]=[CH:... | NO | CCOc1cc([C@@H](CC(=O)O)N2Cc3c(Cl)ccc(NC(=O)C4CC4)c3C2=O)ccc1OC | null | Cl | O=C(n1ccnc1)n1ccnc1 | 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 | 25 | 2 | To a solution of (3R)-3-[4-chloro-7-(cyclopropanecarbonyl-amino)-1-oxo-1,3-dihydro-isoindol-2-yl]-3-(3-ethoxy-4-methoxy-phenyl)-propionic acid (1.3 g, 2.8 mmol) in tetrahydrofurane (10 ml) was added carbonyldiimidazole (0.7 g, 4.2 mmol) at room temperature. The solution was stirred for 2 hours at room temperature. To t... | CCOc1cc([C@@H](CC(=O)NO)N2Cc3c(Cl)ccc(NC(=O)C4CC4)c3C2=O)ccc1OC | null | 87.8 | null |
709,946 | ord_dataset-c8069773c1a148aca8ab417108daacc5 | null | 2006-01-01T00:05:00 | true | [CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([C:10]2([C:14]2[CH:15]=[C:16]([NH2:20])[CH:17]=[CH:18][CH:19]=2)[CH3:13])[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].N1C=CC=CC=1.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>ClCCl>[CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([C:10]2([C:14]2[CH:15]=[C:16]([NH:20][S:28]([CH3:27])(=[O:30])=[O:29])[CH:1... | CS(=O)(=O)Cl | CCCCCCN1CC2C(C1)C2(C)c1cccc(N)c1 | 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 | 48 | To a solution of 3-(3-hexyl-6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenylamine (Preparation 12, 200 mg, 0.735 mmol) in dichloromethane (5 ml) at room temperature was added pyridine (0.15 ml, 1.84 mmol) then dropwise over 5 minutes methanesulfonylchloride (0.11 ml, 158 mg, 1.38 mmol). The mixture was stirred for 48 h, con... | CCCCCCN1CC2C(C1)C2(C)c1cccc(NS(C)(=O)=O)c1 | null | 82.3 | null |
673,539 | ord_dataset-632f0d9054ce41aba87d4970966c34a6 | null | 2005-01-01T00:06:00 | true | [NH:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)[C:2]([CH3:4])=[O:3].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]([O:22][CH3:23])=[O:21]>CC(C)=O>[NH:1]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:7][CH:6]=1)[C:2]([CH3:4])=[O:3] | COC(=O)CBr | CC(=O)Nc1ccc(O)cc1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | null | null | null | null | null | null | null | null | null | null | 25 | null | 4-Acetaminophenol (1.51 g), potassium carbonate (1.38 g) and methyl bromoacetate (1.0 ml) were combined in acetone (40 ml) and heated to reflux for 5 hours. The mixture was allowed to cool to room temperature, filtered and evaporated. The residue was dissolved in ethyl acetate, washed with water and then with brine the... | COC(=O)COc1ccc(NC(C)=O)cc1 | null | null | null |
427,817 | ord_dataset-8cce6f317d644b348a7978a2dce3ea01 | null | 1999-01-01T00:03:00 | true | [CH3:1][N:2]([CH2:4][CH2:5][O:6][C:7]1[C:20]2[C:19]([C:21]([O:23]CCN(C)C)=[O:22])=[C:18]3[C:13]([CH:14]=[C:15]4[CH:32]=[CH:31][CH:30]=[CH:29][C:16]4=[CH:17]3)=[N:12][C:11]=2[CH:10]=[CH:9][CH:8]=1)[CH3:3]>[OH-].[Na+].CO>[CH3:3][N:2]([CH2:4][CH2:5][O:6][C:7]1[C:20]2[C:19]([C:21]([OH:23])=[O:22])=[C:18]3[C:13]([CH:14]=[C:... | CN(C)CCOC(=O)c1c2cc3ccccc3cc2nc2cccc(OCCN(C)C)c12 | null | null | [Na+] | [OH-] | 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 | A solution of N,N-dimethylaminoethyl 2-(N,N-dimethylamino)ethoxy-benz[b]acridine-12-carboxylate (86 mg, 0.20 mmol ) in 4N sodium hydroxide (7.3 ml) and methanol (22 ml) was stirred at 65° C. for 1 hour and at 35° C. for 15 hours. The reaction mixture was evaporated under reduced pressure to dryness. The residue was was... | CN(C)CCOc1cccc2nc3cc4ccccc4cc3c(C(=O)O)c12 | null | 31.9 | null |
1,550,125 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[C:17]2[C:12](=[C:13]([Cl:18])[CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]([OH:19])[N:9]=1.Br[CH2:21][CH2:22][O:23][CH3:24]>O>[Cl:7][C:8]1[C:17]2[C:12](=[C:13]([Cl:18])[CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]([O:19][CH2:21][CH2:22][O:23][CH3:24])[N:9]=1 | COCCBr | Oc1cc2c(Cl)cccc2c(Cl)n1 | null | O=C([O-])[O-] | [K+] | 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 | 50 | null | Potassium carbonate (646 mg, 4.67 mmol) was added to a solution of 1,5-dichloroisoquinolin-3-ol (500 mg, 2.336 mmol) and 1-bromo-2-methoxyethane (357 mg, 2.57 mmol) and heated to 50° C. for 3 hrs. After 3 hrs the reaction was diluted with water and extracted with EtOAc (2×). The organic layer was washed with water foll... | COCCOc1cc2c(Cl)cccc2c(Cl)n1 | null | 86.5 | null |
1,271,400 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [Na].Cl[C:3]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([F:16])([F:15])[F:14])=[CH:10][CH:11]=2)[N:6]=[C:5]([S:17][CH2:18][CH3:19])[C:4]=1[C:20]([NH:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=1)=[O:21].CCCCCC.[CH3:37][OH:38]>>[CH2:18]([S:17][C:5]1[C:4]([C:20]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26... | CO | CCSc1nc2cc(C(F)(F)F)ccc2c(Cl)c1C(=O)NCc1cccc(F)c1 | null | [Na] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCCC | null | null | null | null | null | null | null | null | null | null | 60 | null | 20 mg (0.95 mmol) sodium were added to methanol (6 ml) at RT. Once the sodium had completely dissolved, a solution of 210 mg (0.47 mmol) 4-chloro-2-ethylsulfanyl-N-[(3-fluorophenyl)-methyl]-7-(trifluoromethyl)-quinoline-3-carboxamide (example 122) in MeOH (2 ml) was added at RT. The mixture was then heated for 30 min a... | CCSc1nc2cc(C(F)(F)F)ccc2c(OC)c1C(=O)NCc1cccc(F)c1 | null | 38 | null |
700,062 | ord_dataset-bbd7e53f000345838ad4920a07a169ff | null | 2006-01-01T00:03:00 | true | [Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[CH2:30]([O:37][C:38](=[O:49])[N:39]([C@H:41]1[CH2:46][CH2:45][C@H:44]([CH:47]=O)[CH2:43][CH2:42]1)[CH3:40])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C1COCC1>[CH2:30]([O:37][C:38](=[O:49])[N:39]([CH:41]1[CH2:46][CH2:45][CH:44]([CH... | COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1 | CN(C(=O)OCc1ccccc1)[C@H]1CC[C@H](C=O)CC1 | null | CC(C)(C)[O-] | [Cl-] | [K+] | 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 | 0.5 | A supension of 128.6 g (375 mmol) of (methoxymethyl)triphenylphosphonium chloride in 540 ml THF was treated at −8° C. with 43.1 g (375 mmol) potassium tert-butoxide. The red solution was stirred 30 min at 0° C. and cooled (−20° C.), then 82.6 g (300 mmol) of trans-(4-Formyl-cyclohexyl)-methyl-carbamic acid benzyl ester... | COC=CC1CCC(N(C)C(=O)OCc2ccccc2)CC1 | null | null | null |
580,059 | ord_dataset-60f3171f0342452f8814e7f294e2be8b | null | 2003-01-01T00:02:00 | true | [NH2:1][C:2]1[CH:24]=[CH:23][C:5]2[CH:6]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH2:7][CH2:8][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:10][C:4]=2[CH:3]=1.Cl[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=1)=[O:27].C(N(CC)CC)C>C(Cl)Cl>[C:14]([O:13][C:11]... | O=C(Cl)OCc1ccc([N+](=O)[O-])cc1 | COC(=O)CC1CCN(C(=O)OC(C)(C)C)Cc2cc(N)ccc21 | null | null | null | 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 | 5 | To a stirring solution of methyl 2-{8-amino-2-[(tert-butyl)oxycarbonyl]-1H,3H,4H,5H-benzo[e]azepin-5-yl}acetate (1 eq) in methylene chloride (0.1 M) was added 4-nitrobenzyl chloroformate (1.1 eq) and triethylamine (5 eq) at room temperature. After stirring for 5 hr, the reaction mixture was diluted with methylene chlor... | COC(=O)CC1CCN(C(=O)OC(C)(C)C)Cc2cc(NC(=O)OCc3ccc([N+](=O)[O-])cc3)ccc21 | null | null | null |
460,514 | ord_dataset-aa5bc55d09b7465ab353e144a7ac3ad1 | null | 2000-01-01T00:03:00 | true | [O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH:7]1[NH:11][C:10](=[O:12])[CH2:9][CH:8]1[C:13]([F:16])([F:15])[F:14].F[B-](F)(F)F.[CH3:22][O+](C)C>C(Cl)Cl>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH:7]1[CH:8]([C:13]([F:16])([F:14])[F:15])[CH2:9][C:10]([O:12][CH3:22])=[N:11]1 | C[O+](C)C | O=C1CC(C(F)(F)F)C(CC2OCCO2)N1 | null | F[B-](F)(F)F | 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 | The product material from Example 223 B is treated with trimethyloxonium tetrafluoroborate in DCM by the method of Example 3 to yield 2-[(1,3-dioxolan-2-yl)methyl]-3,4-dihydro-5-methoxy-3-(trifluoromethyl)-2H-pyrrole as a mixture of diastereomers. | COC1=NC(CC2OCCO2)C(C(F)(F)F)C1 | null | null | null |
1,724,107 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | [CH3:1][C:2]1[O:6][C:5]([CH2:7][NH:8][C:9]([C:11]2[C:16](=[O:17])[C:15](Br)=[C:14]([CH3:19])[N:13]([CH:20]3[CH2:23][CH2:22][CH2:21]3)[CH:12]=2)=[O:10])=[N:4][N:3]=1.[F:24][C:25]([F:36])([F:35])[C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH3:1][C:2]1[O:6][C:5]([CH2:7][NH:8][C:9... | Cc1nnc(CNC(=O)c2cn(C3CCC3)c(C)c(Br)c2=O)o1 | OB(O)c1cccc(C(F)(F)F)c1 | null | O=C([O-])[O-] | [K+] | 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 | 75 | 18 | To a solution of 5-bromo-1-cyclobutyl-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid (5-methyl-[1,3,4]oxadiazol-2-ylmethyl)-amide (preparation 24, 44 mg, 0.115 mmol), 3-(trifluoromethyl)phenyl-boronic acid (26 mg, 0.137 mmol), 1,1′-[bis(diphenylphosphino)ferrocene]dichloropalladium(II) (13 mg, 0.018 mmol) in ace... | Cc1nnc(CNC(=O)c2cn(C3CCC3)c(C)c(-c3cccc(C(F)(F)F)c3)c2=O)o1 | null | null | null |
1,257,169 | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | null | 2013-01-01T00:02:00 | true | [CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:35][CH3:36])=[C:10]([CH2:19][NH:20][C:21](=[O:34])[C:22]3[CH:27]=[CH:26][C:25]([C:28]#[C:29][CH2:30][CH2:31][CH2:32][OH:33])=[CH:24][CH:23]=3)[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2]>C1COCC1.CO.[OH-].[OH-].[Pd+2]>[CH2:1]([N:3]1[C:7]2... | CCc1nc2c(cnn2CC)c(NC2CCOCC2)c1CNC(=O)c1ccc(C#CCCCO)cc1 | null | null | [Pd+2] | [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 | null | Pd(OH)2 (200 mg) was added to a solution of Intermediate 32 (200 mg, 0.40 mmol) in THF/MeOH (5 mL each). The solution was treated with H2 at ambient pressure for 3 h. The reaction mixture was then filtered through a plug of celite. The plug was washed with MeOH (50 mL) and the solvent was concentrated in vacuo to affor... | CCc1nc2c(cnn2CC)c(NC2CCOCC2)c1CNC(=O)c1ccc(CCCCCO)cc1 | null | 101.3 | null |
1,692,460 | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | null | 2016-01-01T00:02:00 | true | [OH:1][C:2]1[CH:11]=[CH:10][C:9]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].Br[CH2:18][CH:19]1[CH2:21][CH2:20]1.C([O-])([O-])=O.[K+].[K+].Cl>CC#N>[CH:19]1([CH2:18][N:12]([C:9]2[CH:10]=[CH:11][C:2]([OH:1])=[C:3]([CH:8]=2)[C:4]([O:6][CH3:7])=[O:5])[S:13]([CH3:16])(=[O:15])=[O:14])[CH2... | BrCC1CC1 | COC(=O)c1cc(NS(C)(=O)=O)ccc1O | null | Cl | O=C([O-])[O-] | [K+] | 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 | 25 | 96 | To a solution of methyl 2-hydroxy-5-(methylsulfonamido)benzoate (6.8 g, 27.72 mmol) in CH3CN (200 ml), (bromomethyl)cyclopropane (5.62 g, 41.58 mmol) and K2CO3 (7.66 g, 55.4 mmol) were added, and the reaction was stirred at RT for 4 days. The reaction mixture was poured into ice-water (400 ml), acidified with HCl 36% (... | COC(=O)c1cc(N(CC2CC2)S(C)(=O)=O)ccc1O | null | 73.3 | null |
1,532,067 | ord_dataset-8d5c200bca27407ab9febe7598e16458 | null | 2015-01-01T00:01:00 | true | [NH2:1][C:2](=[O:27])[CH:3]([CH3:26])[C@H:4]([NH:18]C(=O)OC(C)(C)C)[C:5]1[NH:9][C:8]2[CH:10]=[CH:11][C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:13][C:7]=2[N:6]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:18][C@H:4]([C:5]1[NH:9][C:8]2[CH:10]=[CH:11][C:12]([C:14]([CH3:15])([CH3:17])[CH3:16])=[CH:13][C:7]=2[N:6]=1)[C@@H:3]([CH3:26... | CC(C(N)=O)[C@H](NC(=O)OC(C)(C)C)c1nc2cc(C(C)(C)C)ccc2[nH]1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | null | null | A solution of tert-butyl [(1S)-3-amino-1-(5-tert-butyl-1H-benzimidazol-2-yl)-2-methyl-3-oxopropyl]carbamate (Preparation 29, 3.07 g, 8.2 mmol) in DCM (50 mL) and TFA (10 mL) was stirred at room temperature for 3 hours before concentrating in vacuo. Saturated aqueous NaHCO3 solution (100 mL) was added and the product ex... | C[C@@H](C(N)=O)[C@H](N)c1nc2cc(C(C)(C)C)ccc2[nH]1 | null | null | null |
248,392 | ord_dataset-75ca79f43dad4cc8a934fe6487fa8eb1 | null | 1992-01-01T00:05:00 | true | Cl.[NH2:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[Cl:9][C:10]1[C:15]([C:16]([C:18]2[CH2:22][CH2:21][CH2:20][C:19]=2N2CCCC2)=[O:17])=[CH:14][CH:13]=[CH:12][N:11]=1.C(O)(C)(C)C>C(N(CC)CC)C>[Cl:9][C:10]1[C:15]([C:16]([C:18]2[CH2:22][CH2:21][CH2:20][C:19]=2[NH:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])=[O:17])=[CH:14][CH:... | CCOC(=O)CN | O=C(C1=C(N2CCCC2)CCC1)c1cccnc1Cl | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CC(C)(C)O | null | null | null | null | null | null | null | null | null | null | null | Add equimolar amounts of ethyl glycinate hydrochloride, triethylamine, and (2-chloro-3-pyridinyl)[2-(1-pyrrolidinyl)-1-cyclopenten-1-yl]methanone to t-butyl alcohol (170 ml per 0.020 mole of amine). Reflux the resulting mixture for 34 hrs, monitoring the reaction by thin-layer chromatography as needed. Cool the reactio... | CCOC(=O)CNC1=C(C(=O)c2cccnc2Cl)CCC1 | null | null | null |
661,337 | ord_dataset-04d607efe1d9485eb99fafa06880f62e | null | 2005-01-01T00:02:00 | true | C[O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11]/[C:12](=[C:19]1\[C:20](=[O:28])[NH:21][C:22]2[C:27]\1=[CH:26][CH:25]=[CH:24][CH:23]=2)/[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:4].O1CCOCC1.[OH-].[Na+].Cl>CO>[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11]/[C:12](=[C:19]1\[C:20](=[O:28])[NH:21]... | COC(=O)c1ccccc1N/C(=C1\C(=O)Nc2ccccc21)c1ccccc1 | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | CO | null | null | null | null | null | null | null | null | null | 80 | 2 | 176 mg (0.48 mmol) of (Z)-3-[1-(2-methoxycarbonyl-phenylamino)-1-phenyl-methylidene]-2-indolinone are dissolved in 15 ml of methanol and 2 ml of dioxane and after the addition of 1.4 ml of 1N sodium hydroxide solution stirred for two hours at 80° C. Then the mixture is neutralised 1.4 ml of 1N hydrochloric acid while b... | O=C1Nc2ccccc2/C1=C(/Nc1ccccc1C(=O)O)c1ccccc1 | null | null | null |
702,346 | ord_dataset-c408dfed796e4354b61e312e67f7143f | null | 2006-01-01T00:04:00 | true | [NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[NH:7])=[CH:4][C:3]=1[O:11][CH3:12].[Cl:13][C:14]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:15]=1[CH:16]=[C:17]([C:20]#[N:21])[C:18]#[N:19]>>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[N:8]=[C:18]([NH2:19])[C:17]([CH2:20][NH2:21])=[C:16]([C:15]3[CH:22]=[CH:23][C:24]([Cl:26])=[... | COc1cc(C(=N)N)ccc1N | N#CC(C#N)=Cc1ccc(Cl)cc1Cl | 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, MS: m/e=389.9 (M+H+), was prepared from 4-amino-3-methoxy-benzamidine and 2-(2,4-dichloro-benzylidene)-malononitrile in analogy to the process described in Example 11 as a solid. | COc1cc(-c2nc(N)c(CN)c(-c3ccc(Cl)cc3Cl)n2)ccc1N | null | null | null |
306,621 | ord_dataset-a6643d22de674f30a85ba57198b82644 | null | 1995-01-01T00:03:00 | true | [ClH:1].[NH2:2][CH2:3][CH2:4][C:5]1[CH:16]=[CH:15][C:8]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:6]=1.Cl.[N+](C1C=CC([C:27]2[CH:35]=[C:34]([NH:36][C:37]([NH2:39])=[NH:38])[CH:33]=[CH:32][C:28]=2[C:29](O)=[O:30])=CC=1)([O-])=O.C(N(CC)CC)C>CN(C)C=O>[ClH:1].[NH:36]([C:34]1[CH:35]=[CH:27][C:28]([C:29]([NH:2]... | N=C(N)Nc1ccc(C(=O)O)c(-c2ccc([N+](=O)[O-])cc2)c1 | COC(=O)CCc1ccc(CCN)cc1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 5 | A mixture of 486 mg of methyl 4-(2-aminoethyl)hydrocinnamate hydrochloride, 672 mg of 4-nitrophenyl-4-guanidino-benzoate hydrochloride, 404 mg of triethylamine and 10 ml of dimethylformamide was stirred at room temperature under argon for 5 hours. The reaction mixture was then evaporated to dryness in vacuo, and the re... | COC(=O)CCc1ccc(CCNC(=O)c2ccc(NC(=N)N)cc2)cc1 | null | 64.4 | null |
524,544 | ord_dataset-293186f5c9b441cab57f03cd3a18ac26 | null | 2001-01-01T00:11:00 | true | [H-].[Na+].[Br:3][C:4]1[C:5]([OH:18])=[CH:6][C:7]2[C:8]([CH3:17])([CH3:16])[CH2:9][CH2:10][C:11]([CH3:15])([CH3:14])[C:12]=2[CH:13]=1.[CH3:19][O:20][CH2:21][CH2:22][O:23][CH2:24]Cl.O>CN(C=O)C>[CH3:19][O:20][CH2:21][CH2:22][O:23][CH2:24][O:18][C:5]1[C:4]([Br:3])=[CH:13][C:12]2[C:11]([CH3:14])([CH3:15])[CH2:10][CH2:9][C:... | COCCOCCl | CC1(C)CCC(C)(C)c2cc(Br)c(O)cc21 | null | [H-] | [Na+] | 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 | 720 mg (24 mmol) of sodium hydride (80% in oil) and 50 ml of DMF are introduced into a three-necked flask under a stream of nitrogen. A solution of 5.7 g (20 mmol) of 3-bromo-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthol dissolved in 75 ml of DMF are added dropwise and the mixture is stirred until the evolution of ... | COCCOCOc1cc2c(cc1Br)C(C)(C)CCC2(C)C | null | null | null |
292,726 | ord_dataset-b90b48a6c23149a1aa2d91b92b1a31e4 | null | 1994-01-01T00:07:00 | true | [NH2:1][C:2]1[N:6]([CH3:7])[C:5](S)=[N:4][C:3]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10]>[Ni].C(O)C>[NH2:1][C:2]1[N:6]([CH3:7])[CH:5]=[N:4][C:3]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10] | CCOC(=O)c1nc(S)n(C)c1N | null | null | [Ni] | 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 | 2 | A solution of ethyl 5-amino-2-mercapto-1-methylimidazole-4-carboxylate (1.0 g, 5.0 mmol), prepared by the method of Cook, Downer, and Heilbron, J. Chem. Soc. 2028.(1948), and W-2 Raney nickel (2 mL, 50% slurry in water)in ethanol (20 mL) were agitated in an ultrasonic cleaning bath at 50° C. for 1 hour. Sonication was ... | CCOC(=O)c1ncn(C)c1N | null | 95.8 | null |
1,440,626 | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | null | 2014-01-01T00:06:00 | true | [NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([O:13][CH3:14])[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.[C:15](OC(=O)C)(=[O:17])[CH3:16].O>C(OCC)(=O)C>[C:15]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C@@H:9]([O:13][CH3:14])[C:10]([OH:12])=[O:11])=[CH:6][CH:7]=1)(=[O:17])[CH3:16] | CC(=O)OC(C)=O | CO[C@H](Cc1ccc(N)cc1)C(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | O | null | null | null | null | null | null | null | null | null | 90 | 1 | To (R)-(−)-3-(4-aminophenyl)-2-methoxypropionic acid (40 g) in a 0.5 L glass reactor was added ethyl acetate (80 g) and acetic anhydride (62.8 g). The mixture was stirred at 90° C. for 1 hour. Upon cooling, the solvent was removed by vacuum distillation, providing an oily residue. To this residue was added water (120 g... | CO[C@H](Cc1ccc(NC(C)=O)cc1)C(=O)O | null | 53.5 | null |
1,338,085 | ord_dataset-08852243bba44cb28769a5833f1515fe | null | 2013-01-01T00:09:00 | true | [ClH:1].Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([O:9][NH2:10])[CH2:5][CH2:4]1.[CH3:11][C@:12]12[CH2:29][CH2:28][C@H:27]3[C@@H:17]([CH2:18][C:19](=[O:31])[CH:20]4[C@:25]3([CH3:26])[CH2:24][CH2:23][C:22](=O)[CH2:21]4)[C@@H:16]1[CH2:15][CH2:14][C:13]2=[O:32].[Na+].[Cl-]>O.C1COCC1>[ClH:1].[NH:3]1[CH2:8][CH2:7][CH:6]([O:9][N:10]=[C:... | NOC1CCNCC1 | C[C@]12CCC(=O)CC1C(=O)C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12 | null | Cl | [Cl-] | [Na+] | 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 | 2 | To a solution of 4-piperidyloxyamine dihydrochloride (III-a, Prepn. 1, 100 mg) and Na2HPO4.12H2O (380 mg) in water (1.6 mL), a solution of androstane-3,6,17-trione (160 mg) in THF (3.2 mL) was added. After 2 hours at room temperature, NaCl (150 mg) was added and stirred for 15 min. The mixture was extracted with THF (2... | C[C@]12CCC(=NOC3CCNCC3)CC1C(=O)C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12 | null | null | null |
152,188 | ord_dataset-5944a40bb4504bbe8185cfdf2a811d03 | null | 1987-01-01T00:01:00 | true | [CH:1]([CH:4]1[NH:8][C:7](=[O:9])[CH2:6][NH:5]1)([CH3:3])[CH3:2].[OH-].[Na+].[Cl:12][CH:13]([Cl:17])[C:14](Cl)=[O:15]>C(OC)(C)(C)C.O>[Cl:12][CH:13]([Cl:17])[C:14]([N:5]1[CH2:6][C:7](=[O:9])[NH:8][CH:4]1[CH:1]([CH3:3])[CH3:2])=[O:15] | O=C(Cl)C(Cl)Cl | CC(C)C1NCC(=O)N1 | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COC(C)(C)C | O | null | null | null | null | null | null | null | null | null | null | 10 | 45 g (0.35 mole) of 2-isopropyl-4-oxo-imidazolidine (Example 3) were dissolved in 250 ml of methyl tert.-butyl ether, 17.2 g (0.43 mole) of sodium hydroxide in 20 ml of water were added, and 57 g (0.39 mole) of dichloroacetyl chloride were then added dropwise at from 10° to 15° C. The mixture was stirred for 10 hours a... | CC(C)C1NC(=O)CN1C(=O)C(Cl)Cl | null | 49 | null |
1,754,745 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [CH3:1][O:2][C:3]([CH3:7])([CH3:6])[CH2:4][NH2:5].Cl[C:9]1[C:14]2[N:15]=[C:16]([S:19][CH3:20])[N:17]=[CH:18][C:13]=2[CH:12]=[CH:11][N:10]=1>>[CH3:1][O:2][C:3]([CH3:7])([CH3:6])[CH2:4][NH:5][C:9]1[C:14]2[N:15]=[C:16]([S:19][CH3:20])[N:17]=[CH:18][C:13]=2[CH:12]=[CH:11][N:10]=1 | CSc1ncc2ccnc(Cl)c2n1 | COC(C)(C)CN | 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 according to the method described for Preparation 175 using 2-methoxy-2-methylpropan-1-amine and 8-chloro-2-(methylthio)pyrido[3,4-d]pyrimidine (Preparation 33). The residue was purified by elution through an SCX-2 column using 50% methanol in chloroform followed by 50% chloroform in 7N ... | COC(C)(C)CNc1nccc2cnc(SC)nc12 | null | null | null |
1,376,352 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[CH:16]=[C:15](O)[N:14]4[N:18]=[CH:19][CH:20]=[C:13]4[N:12]=3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.CN(C)C1C=CC=CC=1.O=P(Cl)(Cl)[Cl:32]>>[Cl:32][C:15]1[N:14]2[N:18]=[CH:19][CH:20]=[C:13]2[N:12]=[C:11]([CH:8]2[CH2:9][CH2:10][C:5]3([O:4][CH2:3][CH2:2][O:1]3)[CH2:6][CH2:7]2)[CH:16]... | Oc1cc(C2CCC3(CC2)OCCO3)nc2ccnn12 | O=P(Cl)(Cl)Cl | 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 | 25 | 18 | 5-(1,4-dioxaspiro[4.5]decan-8-yl)pyrazolo[1,5-a]pyrimidin-7-ol (Int-5e, 11.7 mmol) was charged to 250 mL round-bottom flask. To this flask was added 4 mL N, N-dimethylaniline, followed by 40 mL POCl3. This suspension was sonicated to break up the starting material and stirred at room temperature for 18 hours. After 18 ... | Clc1cc(C2CCC3(CC2)OCCO3)nc2ccnn12 | null | 77 | null |
146,166 | ord_dataset-4731a430f0af464b83e8b5b145cd2c77 | null | 1986-01-01T00:07:00 | true | [ClH:1].C([NH:4][NH:5][C:6]1[S:7][C:8]2[CH2:14][CH2:13][CH2:12][CH2:11][C:9]=2[N:10]=1)=O>C(O)C.Cl>[ClH:1].[NH:5]([C:6]1[S:7][C:8]2[CH2:14][CH2:13][CH2:12][CH2:11][C:9]=2[N:10]=1)[NH2:4] | O=CNNc1nc2c(s1)CCCC2 | null | 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 | null | A solution of 40.2 g of 1-formyl-2-(4,5,6,7-tetrahydro-benzothiazolyl)-hydrazine hydrochloride in 400 ml of ethanol and 100 ml of concentrated hydrochloric acid is boiled under reflux for 4 hours. Concentration of the mixture and drying of the residue gives 41.5 g of 2-hydrazino-4,5,6,7-tetrahydro-benzothiazole hydroch... | NNc1nc2c(s1)CCCC2 | null | 117.3 | null |
1,601,206 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [NH2:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[N:5]=[N:4][C:3]=1[C:16]([NH2:18])=[O:17].[C:19](=O)(OCC)[O:20]CC.[O-]CC.[Na+]>C(O)C>[CH3:15][O:14][C:11]1[CH:10]=[CH:9][C:8]([CH2:7][N:6]2[C:2]3[NH:1][C:19](=[O:20])[NH:18][C:16](=[O:17])[C:3]=3[N:4]=[N:5]2)=[CH:13][CH:12]=1 | COc1ccc(Cn2nnc(C(N)=O)c2N)cc1 | CCOC(=O)OCC | null | CC[O-] | [Na+] | 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 5-Amino-1-(4-methoxybenzyl)-1H-1,2,3-triazole-4-carboxamide (example 1, step a) (7.59 g, 30.7 mmol), diethyl carbonate (4.72 g, 39.9 mmol) and sodium ethoxide (3.76 g, 55.3 mmol) in ethanol (97.1 mL) was heated to reflux overnight. The solid was filtered, washed with EtOH and dried to give 3-(4-methoxybenz... | COc1ccc(Cn2nnc3c(=O)[nH]c(=O)[nH]c32)cc1 | null | 50.9 | null |
817,327 | ord_dataset-50f99930fc41474db226bc80774b38df | null | 2008-01-01T00:04:00 | true | Br[C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[O:12][C:11]([CH3:14])([CH3:13])[N:10]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@@H:9]2[CH2:22][F:23])=[CH:4][CH:3]=1.[CH3:24][S:25]SC.[Cl-].[NH4+].C(OCC)(=O)C>O1CCCC1>[C:18]([O:17][C:15]([N:10]1[C@H:9]([CH2:22][F:23])[C@@H:8]([C:5]2[CH:6]=[CH:7][C:2]([S:25][CH3:24])=... | CC(C)(C)OC(=O)N1[C@H](CF)[C@@H](c2ccc(Br)cc2)OC1(C)C | CSSC | null | [Cl-] | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 25 | 0.5 | N-butyl lithium (n-BuLi), (1.78 g, 28 mmol, 1.2 eq) was added to a solution of tert-butyl (4S,5R)-5-(4-bromophenyl)-4-(fluoromethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (9.0 g, 23 mmol) in 30 ml of anhydrous tetrahydrofuran (THF) at −78° C. in 30 min, and the reaction mixture was stirred for 30 minutes under N2.... | CSc1ccc([C@H]2OC(C)(C)N(C(=O)OC(C)(C)C)[C@@H]2CF)cc1 | null | null | null |
61,764 | ord_dataset-d9fb402fe3e745c1893a29161cc5dda2 | null | 1980-01-01T00:01:00 | true | [CH:1]([N:14]1[C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][N:16]=[CH:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23]=[O:24]>>[CH:1]([N:14]1[C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][N:16]=[C:15]1[CH2:23][OH:24])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:... | COC(=O)c1cncn1C(c1ccccc1)c1ccccc1 | C=O | 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 | 2.9 g (0.01 mol) of 1-benzhydryl-5-methoxycarbonyl-imidazole (Example 8) and 25 cc of 50% methanolic formaldehyde solution were heated for 36 hours to 135° C. 3.15 g of 1-benzhydryl-2-hydroxymethyl-5-methoxycarbonyl-imidazole, m.p. 160° C., were obtained from the reaction mixture in an almost quantitative yield. | COC(=O)c1cnc(CO)n1C(c1ccccc1)c1ccccc1 | null | null | null |
1,335,029 | ord_dataset-08852243bba44cb28769a5833f1515fe | null | 2013-01-01T00:09:00 | true | C([O:8][C:9]1[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:10]=1[O:11][CH2:12][CH:13]1[CH2:15][O:14]1)C1C=CC=CC=1.C([SiH](CC)CC)C>[Pd].C(O)C>[F:20][C:19]1[CH:18]=[CH:17][CH:16]=[C:10]([O:11][CH2:12][CH:13]2[CH2:15][O:14]2)[C:9]=1[OH:8] | Fc1cccc(OCC2CO2)c1OCc1ccccc1 | null | null | [Pd] | CC[SiH](CC)CC | 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 | 25 | 16 | To a mixture of 2-{[2-(benzyloxy)-3-fluorophenoxy]methyl}oxirane (8 g, 29.2 mmol), ethanol (65 ml) and Pd/C (0.5 g) under N2, triethylsilane (9.3 ml, 58.2 mmol) was added dropwise. The solution was stirred for 16 h at room temperature and filtered through Celite. The solvent was evaporated, Na2CO3 (10%) was added and t... | Oc1c(F)cccc1OCC1CO1 | null | 65.1 | null |
832,319 | ord_dataset-47bd90bf5ec74fcd99ce250a56e18c8f | null | 2008-01-01T00:07:00 | true | C([CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:12]([I:15])=[CH:11][C:7]=1[C:8]([OH:10])=O)(O)=O.[C:16](OC(=O)C)(=[O:18])[CH3:17].C([O-])(=O)C.[Na+].C(O)(=O)C>O>[I:15][C:12]1[CH:13]=[CH:14][C:6]2[O:5][CH:4]=[C:8]([O:10][C:16](=[O:18])[CH3:17])[C:7]=2[CH:11]=1 | O=C(O)COc1ccc(I)cc1C(=O)O | CC(=O)OC(C)=O | null | CC(=O)[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(=O)O | null | null | null | null | null | null | null | null | null | 140 | 5 | Place 2-carboxymethoxy-5-iodo-benzoic acid (Preparation 21a; 7 g, 21 mmol) acetic anhydride (35 ml), sodium acetate (4 g), and acetic acid (5 mL) into a 50 mL round bottom flask. Heat the resulting mixture at 140° C. under stirring for 5 h and cool to room temperature. Add water (12 mL) into the mixture gradually maint... | CC(=O)Oc1coc2ccc(I)cc12 | null | 95 | null |
341,170 | ord_dataset-4c84bc8a34e1469aa1b156355c91cdcc | null | 1996-01-01T00:10:00 | true | [C:1]([NH:8][NH:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1)([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:2].[CH3:17][N:18]=[C:19]=[S:20]>C(O)C>[C:1]([NH:8][NH:9][C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:19]([NH:18][CH3:17])=[S:20])=[CH:14][CH:15]=1)([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:2] | CCOC(=O)C(=O)NNc1ccc(N)cc1 | CN=C=S | null | null | 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 | 8.9 g of 1-ethoxalyl-2-(4-aminophenyl)hydrazine and 3.0 g of methyl isothiocyanate were added to 75 ml of ethanol, followed by refluxing for 3.5 hours under heating. The refluxed product was left to stand for cooling and the precipitated crystal was collected by filtration, washed with ethanol and then dried to obtain ... | CCOC(=O)C(=O)NNc1ccc(NC(=S)NC)cc1 | null | 72.8 | null |
562,079 | ord_dataset-7c28974b7fcf4c9c86d5f2a42ba328a2 | null | 2002-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:14]=[C:13]([O:15][CH2:16][CH:17]=[C:18]([Cl:20])[Cl:19])[CH:12]=[C:11]([Cl:21])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=O.Cl.[NH2:23][OH:24].Cl>N1C=CC=CC=1>[Cl:1][C:2]1[CH:14]=[C:13]([O:15][CH2:16][CH:17]=[C:18]([Cl:20])[Cl:19])[CH:12]=[C:11]([Cl:21])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=... | O=CCCCCOc1c(Cl)cc(OCC=C(Cl)Cl)cc1Cl | NO | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | 25 | 24 | To a mixture of 5.58 g of 5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentanal and 50 ml of pyridine was added 1.25 g of hydroxylamine hydrochloride. After stirring at room temperature for 24 hours, the reaction mixture was poured into diluted hydrochloric acid, and extracted twice with diethyl ether. The die... | ON=CCCCCOc1c(Cl)cc(OCC=C(Cl)Cl)cc1Cl | null | 42 | null |
660,698 | ord_dataset-04d607efe1d9485eb99fafa06880f62e | null | 2005-01-01T00:02:00 | true | [Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7]([CH3:13])([CH3:12])[CH2:6][C:5]2([CH3:15])[CH3:14].[CH2:16]([O:18]CC)C>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH:16]=[O:18])[CH:11]=1)[O:8][C:7]([CH3:13])([CH3:12])[CH2:6][C:5]2([CH3:15])[CH3:14] | CC1(C)CC(C)(C)c2cc(Br)ccc2O1 | CCOCC | null | Cl[Ti](Cl)(Cl)Cl | 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 | 25 | null | A stirred, cooled (ice bath) solution of 6-bromo-2,2,4,4-tetramethyl chroman, (0.5 g, 1.865 mmol) in anhydrous dichloromethane (5 mL) was treated with a 1M solution (1.86 mL, 1.86 mmol) of titanium tetrachloride in dichloromethane followed by α,α-dichloro methyl ether (0.214 g, 1.865 mmol). The reaction mixture was all... | CC1(C)CC(C)(C)c2cc(Br)cc(C=O)c2O1 | null | 94 | null |
1,635,201 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:19]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)=[CH:18][N:17]([CH2:26][CH2:27][F:28])[N:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>CCOC(C)=O.CCO.[Pd]>[F:28][CH2:27][CH2:26][N:17]1[CH:18]=[C:19]([C:20]2[CH:21]=[CH:22][N:23]=[CH:24][CH:25]=2)[C:15]([C:12]2[CH:13]=[CH:14][C:9]([OH:... | FCCn1cc(-c2ccncc2)c(-c2ccc(OCc3ccccc3)cc2)n1 | null | 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 | 18 | Pd/C (1 g) was added to a solution of Intermediate 3B, 4-(3-(4-(benzyloxy)phenyl)-1-(2-fluoroethyl)-1H-pyrazol-4-yl)pyridine (2.1 g) in EtOAc/EtOH (30 mL+30 mL). The mixture was stirred in autoclave at 2.5 atm H2 for 18 h. Pd/C was filtered off and the filtrate was concentrated under reduced pressure to yield the crude... | Oc1ccc(-c2nn(CCF)cc2-c2ccncc2)cc1 | null | 91.6 | null |
752,469 | ord_dataset-844a22e1fcab44a5b59c5e2922b2855a | null | 2007-01-01T00:01:00 | true | C[O:2][C:3]([C:5]1[CH:6]=[C:7]([O:11][CH:12]([CH2:23][CH3:24])[C:13]([NH:15][C:16]([CH3:22])([CH3:21])[C:17]#[C:18][CH2:19][CH3:20])=[O:14])[CH:8]=[N:9][CH:10]=1)=[O:4].[OH-].[Na+]>CC(O)C.O>[C:3]([C:5]1[CH:6]=[C:7]([O:11][CH:12]([CH2:23][CH3:24])[C:13]([NH:15][C:16]([CH3:22])([CH3:21])[C:17]#[C:18][CH2:19][CH3:20])=[O:... | CCC#CC(C)(C)NC(=O)C(CC)Oc1cncc(C(=O)OC)c1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(C)O | null | null | null | null | null | null | null | null | null | null | 1.5 | The product from Stage 2 (2.18 g) was dissolved in propan-2-ol (25 ml) and a solution of sodium hydroxide (0.28 g) in water (10 ml) was added at ambient temperature. The mixture was stirred for 1.5 hours, stored at ambient temperature for 18 hours and evaporated under reduced pressure to remove the propan-2-ol. The res... | CCC#CC(C)(C)NC(=O)C(CC)Oc1cncc(C(=O)O)c1 | null | null | null |
1,356,588 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | [CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:22])[CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:9][C:10]1[CH:11]=[CH:12][C:13]([C:16](=[O:22])[CH2:17][CH2:18][C:19]([O:21][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2... | BrCc1ccccc1 | O=C(O)CCC(=O)c1ccc(Br)cc1 | 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 | null | null | null | null | null | null | null | null | null | null | null | 18 | Benzyl bromide (9.98 g, 58.3 mmol) was added to a solution of 4-(4-bromophenyl)-4-oxobutanoic acid (15.0 g, 58.3 mmol) and K2CO3 (3.5 g, 58.3 mmol) in DMF (300 mL) and stirred for 18 hours. The reaction mixture was partitioned between water (200 mL) and ethyl acetate (500 mL). Sat'd NaHCO3 soln (20 mL) was added and th... | O=C(CCC(=O)c1ccc(Br)cc1)OCc1ccccc1 | null | 79 | null |
75,779 | ord_dataset-8868acadaee548d5802e504148fc3b63 | null | 1981-01-01T00:01:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[NH2:6].Br[CH:13]([CH:17]([CH3:19])[CH3:18])[C:14]([OH:16])=[O:15].[I-].[K+]>CN(P(N(C)C)(N(C)C)=O)C>[CH3:11][O:10][C:8]1[CH:7]=[C:5]([NH:6][C@H:13]([C:14]([OH:16])=[O:15])[CH:17]([CH3:19])[CH3:18])[CH:4]=[C:3]([O:2][CH3:1])[CH:9]=1 | CC(C)C(Br)C(=O)O | COc1cc(N)cc(OC)c1 | null | [I-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)P(=O)(N(C)C)N(C)C | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 3,5-dimethoxyaniline (2.1 g), the m-phenoxybenzyl ester of α-bromoisovaleric acid (1.0 g), potassium iodide (72.9 mg) and 5 ml of HMPT is heated overnight at 70°-80°. The reaction is then worked up by partition between 100 ml of 2 N sulfuric acid and 100 ml of ether. The aqueous phase is extracted with eth... | COc1cc(N[C@H](C(=O)O)C(C)C)cc(OC)c1 | null | null | null |
1,091,229 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:10]([CH3:18])=[C:11]([CH2:16][OH:17])[CH:12]=[N:13][C:14]=2[CH3:15])[CH:5]=[CH:4][N:3]=1.[OH-].[Na+].[O-:21][Mn](=O)(=O)=O.[K+]>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:14]([CH3:15])=[N:13][CH:12]=[C:11]([C:10]=2[CH3:18])[C:16]([OH:21])=[O:17])[CH:5]=[CH:4][N:3]=1 | O=[Mn](=O)(=O)[O-] | Cc1ncc(CO)c(C)c1Oc1ccnc(Cl)c1 | null | [K+] | [Na+] | [OH-] | 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 | (5-(2-chloropyridin-4-yloxy)-4,6-dimethylpyridin-3-yl)methanol (5.00 g, 18.9 mmol) was charged with NaOH (0.1N in H2O, 19 ml, 1.9 mmol). 3% Aqueous KMnO4 (119 ml, 22.7 mmol) was then added. The reaction stirred at room temperature overnight. The solution was diluted with dichloromethane, filtered through celite, and ac... | Cc1ncc(C(=O)O)c(C)c1Oc1ccnc(Cl)c1 | null | 50.5 | null |
1,655,053 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][C:11]#[CH:12])=[CH:5][C:4]=1[O:13][CH3:14].[Li]CCCC.CON(C)[C:23]([C@@H:25]1[CH2:29][CH2:28][CH2:27][N:26]1[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[O:24].[NH4+].[Cl-]>C1COCC1>[CH3:14][O:13][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][C:3]=1[O:2][CH3:1])[O:9][CH2:10... | CON(C)C(=O)[C@@H]1CCCN1C(=O)OC(C)(C)C | C#CCOc1ccc(OC)c(OC)c1 | null | [Cl-] | [Li]CCCC | [NH4+] | 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 | 0.5 | To a THF (50 mL) solution of 1,2-dimethoxy-4-(prop-2-yn-yloxy)benzene (2.118 g), n-BuLi (4.0 mL, 2.64 N hexane solution) was added dropwise at −78° C. and the resulting mixture was stirred at the same temperature for 30 minutes; the reaction mixture was then added dropwise to a solution of (S)-t-butyl 2-(methoxy(methyl... | COc1ccc(OCC#CC(=O)[C@@H]2CCCN2C(=O)OC(C)(C)C)cc1OC | null | 63.8 | null |
18,637 | ord_dataset-8ca24382d55b4303bc34393399f4110e | null | 1977-01-01T00:01:00 | true | [F:1][C:2]([F:9])([F:8])[C:3]([F:7])=[C:4]([F:6])[F:5].[C:10]1([CH3:17])[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[CH:11]=1>>[F:5][C:4]([F:6])([CH:3]([F:7])[C:2]([F:9])([F:8])[F:1])[CH2:17][C:10]1[CH:11]=[C:12]([CH3:16])[CH:13]=[CH:14][CH:15]=1 | Cc1cccc(C)c1 | FC(F)=C(F)C(F)(F)F | 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 | Meta-xylene and hexafluoropropene (3:1 molar ratio), heated at 290° for 3 days, gave 3-(2,2,3,4,4,4-hexafluorobutyl)toluene: ##STR14## in 70% yield based on hexafluoropropene consumed. | Cc1cccc(CC(F)(F)C(F)C(F)(F)F)c1 | null | 70 | null |
306,212 | ord_dataset-a6643d22de674f30a85ba57198b82644 | null | 1995-01-01T00:03:00 | true | [SH:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.Br[CH2:12][CH2:13][N:14]1[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2[C:15]1=[O:24].C(N(CC)CC)C>C(O)C>[C:15]1(=[O:24])[N:14]([CH2:13][CH2:12][S:1][C:2]2[N:7]3[CH:8]=[CH:9][N:10]=[C:6]3[CH:5]=[CH:4][CH:3]=2)[C:18](=[O:19])[C:17]2=[CH:20][C... | O=C1c2ccccc2C(=O)N1CCBr | Sc1cccc2nccn12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 25 | 3 | To a suspension of 5-mercaptoimidazo[1,2-a]pyridine (3.00 g, 20 mmoles) and N-[2-(bromo)ethyl]phthalimide (5.59 g, 22 mmoles) in ethanol (200 ml) was added triethylamine (4.2 ml, 30 mmoles) and the mixture was stirred at room temperature for 3 hours and heated at reflux for 4 hours. After the solvent was distilled off,... | O=C1c2ccccc2C(=O)N1CCSc1cccc2nccn12 | null | 61.1 | null |
1,657,762 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [Br:1][C:2]1[CH:3]=[C:4]([C:8]2([C:11]#[N:12])[CH2:10][CH2:9]2)[CH:5]=[N:6][CH:7]=1.[OH-:13].[NH4+].OO>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([C:11]([NH2:12])=[O:13])[CH2:9][CH2:10]2)[CH:5]=[N:6][CH:7]=1 | [OH-] | N#CC1(c2cncc(Br)c2)CC1 | null | OO | [NH4+] | 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 | 4 | 1-(5-Bromo-pyridin-3-yl)-cyclopropanecarbonitrile (150 mg, 0.672 mmol) is dissolved in THF (1.5 mL) in a reaction vial. Ammonium hydroxide (1 mL) is then added. Hydrogen peroxide (30% aq solution, 0.5 mL) is added slowly. The mixture is stirred at room temperature for 4 h. The volatiles is evaporated to afford 1-(5-bro... | NC(=O)C1(c2cncc(Br)c2)CC1 | null | null | null |
1,749,616 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | [F:1][C:2]1[C:3]([C:18]2[NH:22][C:21]([CH3:23])=[C:20]([C:24]([OH:26])=O)[CH:19]=2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[C:6]([NH:13][C:14]1([CH3:17])[CH2:16][CH2:15]1)=[N:5]2.CC[N:29](C(C)C)C(C)C.N>CN(C=O)C.C(Cl)Cl>[F:1][C:2]1[C:3]([C:18]2[NH:22][C:21]([CH3:23])=[C:20]([C:24]([NH2:29])=[O:26])[CH:19]=2)... | Cc1nc2ccc(F)c(-c3cc(C(=O)O)c(C)[nH]3)c2nc1NC1(C)CC1 | CCN(C(C)C)C(C)C | null | N | 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 | 8 | A mixture of 5-(6-fluoro-2-methyl-3-((1-methylcyclopropyl)amino)quinoxalin-5-yl)-2-methyl-1H-pyrrole-3-carboxylic acid (417c) (0.119 g, 0.336 mmol), 0-(˜7-azabenzotriazol-1-yl)-n,′n,′n,′n′-tetramethyluronium-hexafluorophosphate (GenScript Corporation, 0.160 g, 0.420 mmol), DIPEA (0.146 mL, 0.839 mmol), in DMF (1.679 mL... | Cc1nc2ccc(F)c(-c3cc(C(N)=O)c(C)[nH]3)c2nc1NC1(C)CC1 | null | null | null |
1,032,485 | ord_dataset-83acb82dc5ba4f7aba439b9875aaac43 | null | 2011-01-01T00:02:00 | true | [Br:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[N:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.C[N:17](C=O)C>ClCCl>[Br:1][C:2]1[S:6][C:5]([C:7]([NH2:17])=[O:9])=[N:4][CH:3]=1 | CN(C)C=O | O=C(O)c1ncc(Br)s1 | null | O=C(Cl)C(=O)Cl | 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 | 25 | 1 | To 5-bromo-thiazole-2-carboxylic acid (0.267 g, 0.128 mmol) suspended in dry dichloromethane (30 mL) are added oxalyl chloride (0.22 mL, 0.257 mmol) and a drop of DMF. The reaction is stirred for 1 hour at room temperature. The solvent is evaporated and the resultant crude is dissolved in 7M NE3 in MeOH. The reaction m... | NC(=O)c1ncc(Br)s1 | null | 25 | null |
420,359 | ord_dataset-94e21e9990034c729ea727e7d2ab0eb0 | null | 1998-01-01T00:12:00 | true | [N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9]Cl)=[CH:3][CH:2]=1.[N-:11]=[N+:12]=[N-:13].[Na+]>CS(C)=O.CCOC(C)=O>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][N:11]=[N+:12]=[N-:13])=[CH:3][CH:2]=1 | ClCCCc1ccncc1 | [N-]=[N+]=[N-] | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 65 | null | A solution of 2-3 (7 g, 41.2 mmol) in DMSO (150 mL) was treated with sodium azide (2 g, 45.3 mmol) and heated to 65° C. for 72 h. The solution was diluted with EtOAc, washed with H2O and saturated NaHCO3. The H2O washing was basified to pH11 and extracted with EtOAc. The organic layers were combined, dried with brine a... | [N-]=[N+]=NCCCc1ccncc1 | null | null | null |
425,039 | ord_dataset-1ecf96d88f254270bff816ee7eeffef6 | null | 1999-01-01T00:02:00 | true | [SH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[C:14]([O:18][C:19]([N:21]1[CH2:25][CH2:24][C@@H:23](O)[CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:14]([O:18][C:19]([N:21]1[CH2:25][CH2:24][C@H:23]([S:1][... | CC(C)(C)OC(=O)N1CC[C@@H](O)C1 | CCOC(=O)Cc1ccc(S)cc1 | 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 | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | 20.2 g of ethyl 4-mercaptophenylacetate was dissolved in 450 ml of tetrahydrofuran. With ice cooling and with stirring, 21.0 g of (3R)-1-tert-butoxycarbonyl-3-hydroxypyrrolidine, 29.4 g of triphenylphosphine and 19.5 g of diethyl azodicarboxylate were added to the above solution. The thus prepared mixture was stirred a... | CCOC(=O)Cc1ccc(S[C@H]2CCN(C(=O)OC(C)(C)C)C2)cc1 | null | 18.6 | null |
1,231,991 | ord_dataset-e96f5a2842f14e5380461c234100f05a | null | 2012-01-01T00:12:00 | true | [OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:12])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:19]([O:21][C:22](=[O:27])[CH2:23][CH2:24][CH2:25]Br)[CH3:20]>CN(C=O)C>[CH2:19]([O:21][C:22]([CH2:23][CH2:24][CH2:25][O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:12])=[CH:4][CH:3]=1)=[O:27... | O=C1CCCc2ccc(O)cc21 | CCOC(=O)CCCBr | 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 | null | null | null | null | null | null | null | null | null | null | 25 | 16 | To a suspension of 7-hydroxy-tetralone (0.870 g, 5.3 mmol) and K2CO3 (5 g, excess) in DMF (20 mL) was added ethyl-4-bromobutyrate (0.770 mL, 5.3 mmol) at room temperature and under argon atmosphere. The reaction mixture was stirred at room temperature for ˜16 hours before being poured on ice. The aqueous solution was e... | CCOC(=O)CCCOc1ccc2c(c1)C(=O)CCC2 | null | 80.6 | null |
629,889 | ord_dataset-0a66204fc43e49c2922e6f9107e6b62f | null | 2004-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3=[CH:12][CH:13]=[CH:14][N:9]3[CH2:8][C:7](=O)[C:6]=2[CH:16]=1.[CH2:17]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)[CH3:18]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3=[CH:12][CH:13]=[CH:14][N:9]3[CH:8]=[C:7]([N:22]3[CH2:23][CH2:24][N:19]([CH2:17][CH3:18])[CH2:20][CH2:2... | O=C1Cn2cccc2Sc2ccc(Cl)cc21 | CCN1CCNCC1 | 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 | Starting from 7-chloro-9,10-dihydropyrrolo[2,1-b][1,3]benzothiazepin-9-one (0.19 g, 0.76 mmol) and N-ethylpiperazine (0.70 mL, 6.13 mmol), the title compound was obtained following the above described procedure for (1). After purification, 0.19 g of the desired product were obtained as a white solid (yield 74%). | CCN1CCN(C2=Cn3cccc3Sc3ccc(Cl)cc32)CC1 | null | null | null |
1,136,394 | ord_dataset-aaeaab5f3720492494c1cbbdd0ed2820 | null | 2012-01-01T00:02:00 | true | [OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10]([C:12]2[CH:22]=[C:21]([O:23][C:24]3[CH:29]=[CH:28][C:27]([C:30](=[O:34])[N:31]([CH3:33])[CH3:32])=[C:26]([F:35])[CH:25]=3)[C:15]3[CH2:16][C:17]([CH3:20])([CH3:19])[O:18][C:14]=3[CH:13]=2)=[O:11])=[N:7][CH:8]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH:2... | CN(C)C(=O)c1ccc(Oc2cc(C(=O)Nc3ccc(CO)cn3)cc3c2CC(C)(C)O3)cc1F | null | null | CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21 | 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 | 0 | 1.5 | To a solution of 4-(4-Dimethylcarbamoyl-3-fluoro-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (5-hydroxymethyl-pyridin-2-yl)-amide (145) (88 mg, 0.18 mmol) in 3 mL CH2Cl2 was added Dess-Martin periodinane (93.4 mg, 0.22 mmol) at 0° C. The mixture was stirred at 0° C. for 1.5 hr. The reaction was quenc... | CN(C)C(=O)c1ccc(Oc2cc(C(=O)Nc3ccc(C=O)cn3)cc3c2CC(C)(C)O3)cc1F | null | null | null |
28,549 | ord_dataset-2cb52357eb5f43c2be56ad5c0662f18f | null | 1977-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][C:13]4[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=4[CH:15]=3)[NH:10][N:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:23]I>CC(N(C)C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]3[C:11](=[CH:12][C:13]4[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=4[CH:15]=3)[N:10]([CH3:23])[N:9]=2)=[CH... | CI | Clc1ccc(-c2n[nH]c3cc4ccccc4cc23)cc1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)N(C)C | null | null | null | null | null | null | null | null | null | null | 25 | 1 | To a solution of 14 g of 3-(p-chlorophenyl)-1H-benz[f] indazole dissolved in 150 ml. dry dimethylacetamide under nitrogen is added 3 g. of a 57% suspension of sodium hydride in mineral oil. The reaction mixture is stirred at room temperature for 1 hour and then 5 ml. of methyl iodide is added. Stirring is continued for... | Cn1nc(-c2ccc(Cl)cc2)c2cc3ccccc3cc21 | null | null | null |
1,534,835 | ord_dataset-8d5c200bca27407ab9febe7598e16458 | null | 2015-01-01T00:01:00 | true | [Cl:1][C:2]1[C:7]([C@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2C(OC(C)(C)C)=O)=[CH:6][C:5]([F:20])=[CH:4][N:3]=1.[ClH:21]>O1CCOCC1>[ClH:1].[ClH:21].[Cl:1][C:2]1[C:7]([C@H:8]2[CH2:12][CH2:11][CH2:10][NH:9]2)=[CH:6][C:5]([F:20])=[CH:4][N:3]=1 | CC(C)(C)OC(=O)N1CCC[C@@H]1c1cc(F)cnc1Cl | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 25 | 8 | To a dioxane (5 mL) solution of (R)-tert-butyl 2-(2-chloro-5-fluoropyridin-3-yl)pyrrolidine-1-carboxylate (500 mg, 1.66 mmol) was added HCl (4 N dioxane, 20 mL), followed by stirring at ambient temperature overnight. The mixture was concentrated and treated with Et2O, then vacuum-dried, to provide the product as a whit... | Fc1cnc(Cl)c([C@H]2CCCN2)c1 | null | 80 | null |
1,232,347 | ord_dataset-e96f5a2842f14e5380461c234100f05a | null | 2012-01-01T00:12:00 | true | [H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[C:14]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[C:15]1([C:14]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[CH:5][C:3]#[N:4])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1 | CCOP(=O)(CC#N)OCC | O=C(c1ccccc1)c1ccccc1 | 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 | null | 0.5 | To a suspension of sodium hydride (60% wt in mineral oil) (0.780 g, 32.5 mmol) in THF (100 mL) at room temperature was added diethyl cyanomethylphosphonate (4.50 g, 25.4 mmol) (4 mL). The mixture was stirred for 30 min and benzophenone (4.22 g, 23.2 mmol) was added. The reaction mixture was stirred at room temperature ... | N#CC=C(c1ccccc1)c1ccccc1 | null | null | null |
534,639 | ord_dataset-b1a34bc8c1204d51a772ed27396c794e | null | 2002-01-01T00:02:00 | true | [C:1]1([CH:7]2[CH2:19][C:18](=O)[C:17]3[C:16]4[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=4[NH:10][C:9]=3[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:21]([NH:24][NH2:25])([NH2:23])=[NH:22].[ClH:26].Cl.O>C(O)C>[ClH:26].[NH:24]([N:25]=[C:18]1[C:17]2[C:16]3[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=3[NH:10][C:9]=2[CH2:8][CH:7]([... | N=C(N)NN | O=C1CC(c2ccccc2)Cc2[nH]c3c(c21)CCCC3 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | null | null | A mixture of 2-phenyl-1,2,3,4,5,6,7,8-octahydrocarbazol-4-one (0.8 g), aminoguanidine hydrochloride (0.35 g), concentrated hydrochloric acid (0.15 ml), water (0.15 ml) and ethanol (50 ml) was refluxed for 1 hour. Under reduced pressure, the solvent was evaporated, and to the residue was added sodium hydrogen carbonate ... | N=C(N)NN=C1CC(c2ccccc2)Cc2[nH]c3c(c21)CCCC3 | null | 49.1 | null |
1,064,035 | ord_dataset-ffbef48837674f39816de887b5dc8bae | null | 2011-01-01T00:06:00 | true | [CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][C@H:10]1[CH2:17][CH2:16][CH2:15][C@:12]2([O:14][CH2:13]2)[CH2:11]1>CO>[CH2:1]([NH:8][CH2:13][C@:12]1([OH:14])[CH2:15][CH2:16][CH2:17][C@H:10]([CH3:9])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1 | C[C@H]1CCC[C@@]2(CO2)C1 | NCc1ccccc1 | null | null | 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 | A methanol (1 ml) solution of benzylamine (5.9 g) and (3S,5S)-5-methyl-1-oxaspiro[2.5]octane (3.5 g) were heated in a microwave (100 W) for 30 minutes at 100° C., then concentrated in vacuo and purified by flash column chromatography (SiO2, 20% ethyl acetate/iso-hexane as eluent) to afford the subtitle compound as a co... | C[C@H]1CCC[C@@](O)(CNCc2ccccc2)C1 | null | 69.5 | null |
941,464 | ord_dataset-ed680843f6d14f5c9901869b2a06b4a4 | null | 2010-01-01T00:03:00 | true | [N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Cl:13][C:14]1[CH:15]=[N:16][CH:17]=[C:18]([Cl:33])[C:19]=1[CH2:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[CH:24]=1)=[O:22]>>[Cl:33][C:18]1[CH:17]=[N:16][CH:15]=[C:14]([Cl:13])[C:19]=1/[CH:20]=[C:21](\[O:... | COc1ccc(C(=O)Cc2c(Cl)cncc2Cl)cc1OC | O=C(Cl)c1ccc([N+](=O)[O-])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 | The compound was obtained starting from 4-nitro-benzoyl chloride and 2-(3,5-dichloro-pyridin-4-yl)-1-(3,4-dimethoxy-phenyl)-ethanone, following the procedure of Example 7. | COc1ccc(/C(=C/c2c(Cl)cncc2Cl)OC(=O)c2ccc([N+](=O)[O-])cc2)cc1OC | null | null | null |
1,083,526 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | Cl[C:2]1[N:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[C:9]([F:15])([F:14])[CH2:8][N:7]([CH:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[C:6]=2[N:21]=1.[NH2:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][C:24]=1[CH2:32][CH3:33].Cl>C(O)C>[CH:16]1([N:7]2[CH2:8][C:9]([F:15])([F:14])[C:10](=[O:13])[N:11]([CH3... | CN1C(=O)C(F)(F)CN(C2CCCC2)c2nc(Cl)ncc21 | CCc1cc(C(=O)O)ccc1N | 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 | null | A mixture of 1.1 g (3.481 mmole) of 2-chloro-9-cyclopentyl-7,7-difluoro-5-methyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VII-20), 0.746 g (4.525 mmole) of 4-amino-3-ethylbenzoic acid, 10 mL of ethanol and 40 mL of 1M hydrochloric acid was heated at reflux for 18 hours. The mixture was cooled and the whit... | CCc1cc(C(=O)O)ccc1Nc1ncc2c(n1)N(C1CCCC1)CC(F)(F)C(=O)N2C | null | 22.1 | null |
1,101,263 | ord_dataset-af85e6f81c2d49f08086afd6d9e6959c | null | 2011-01-01T00:10:00 | true | [C:1]([CH2:3][CH:4]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)[C:5](OC)=[O:6])#[N:2]>[Ni].N.CO>[F:15][C:12]1[CH:13]=[CH:14][C:9]([CH:4]2[CH2:3][CH2:1][NH:2][C:5]2=[O:6])=[CH:10][CH:11]=1 | COC(=O)C(CC#N)c1ccc(F)cc1 | null | null | [Ni] | N | 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 | 25 | 17 | Methyl 3-cyano-2-(4-fluorophenyl)propanoate (2.09 g, 10.09 mmol; Example 189A) and 7 M NH3-methanol (100 mL) were added to Raney® nickel, solvent washed (20.90 g, 356 mmol) in a 250 mL stainless steel pressure bottle and stirred for 17 hours under hydrogen at 30 psi and room temperature. The mixture was filtered throug... | O=C1NCCC1c1ccc(F)cc1 | null | null | null |
765,284 | ord_dataset-7a8649d55889427e85b208ae89475895 | null | 2007-01-01T00:04:00 | true | [ClH:1].[OH:2][CH:3]([CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23](OC)=[CH:22][CH:21]=1)[CH2:4][NH:5][C:6]([CH3:17])([CH3:16])[CH2:7][C:8]1[CH:13]=[CH:12][C:11](OC)=[CH:10][CH:9]=1.Cl>C(OCC)C>[ClH:1].[OH:2][CH:3]([CH2:18][O:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH2:4][NH:5][C:6]([CH3:17])([CH3:16])[CH2:7][C:8... | COc1ccc(CC(C)(C)NCC(O)COc2ccc(OC)cc2)cc1 | null | null | Cl | 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 | null | null | Using the method of Example 5, supra, 1,2-epoxy-3-phenoxypropane (600 mg, 4 mmol) and 1,1-dimethyl-2-phenylethylamine (596 mg, 4 mmol) yielded the title compound: GC/EI-MS, m/z (rel. int.) 284 (M+1, 1), 208 (100), 162 (1), 133 (7), 91 (27), 77 (15), 70 (22). The free base in diethyl ether was treated with excess 1M HCl... | CC(C)(Cc1ccccc1)NCC(O)COc1ccccc1 | null | null | null |
470,617 | ord_dataset-f1b9e9741a6a4cc68e7070df811f86bb | null | 2000-01-01T00:07:00 | true | [OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:12]([O:14]CC)=O.[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH2:23])=[CH:20][CH:19]=1>>[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH:23][C:12]([C:3]2[CH:4]=[N:5][C:6]3[C:11]([C:2]=2[OH:1])=[CH:10][CH:9]=[CH:8][CH:7]=3)=[O:14])=[CH:20][CH:19... | NCc1ccc(Cl)cc1 | CCOC(=O)c1cnc2ccccc2c1O | 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 | 200 | 18 | A mixture of 0.50 g of ethyl 4-hydroxy-3-quinolinecarboxylate (J. Amer. Chem. Soc., 68, 1264 (1946)) and 5.0 mL of 4-chlorobenzylamine is stirred 18 h at 200° C. The mixture is cooled to 25° C. and it is diluted with 25 mL of hexanes. After stirring for an additional 1 h the solid precipitate is collected by filtration... | O=C(NCc1ccc(Cl)cc1)c1cnc2ccccc2c1O | null | null | null |
1,295,949 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | [NH:1]1[CH2:5][CH2:4][C@@H:3]([NH:6][C:7]([C:9]2[C:13]3[N:14]=[CH:15][N:16]=[C:17]([C:18]4[C:26]5[O:25][CH2:24][O:23][C:22]=5[CH:21]=[CH:20][C:19]=4[O:27][CH2:28][CH3:29])[C:12]=3[NH:11][CH:10]=2)=[O:8])[CH2:2]1.Cl[C:31]([O:33][CH2:34][CH3:35])=[O:32]>>[CH2:34]([O:33][C:31]([N:1]1[CH2:5][CH2:4][C@@H:3]([NH:6][C:7]([C:9... | CCOC(=O)Cl | CCOc1ccc2c(c1-c1ncnc3c(C(=O)N[C@@H]4CCNC4)c[nH]c13)OCO2 | 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 | Starting from 4-(5-ethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (R)-pyrrolidin-3-ylamide (example A176) and ethyl chloroformate the title compound was obtained as colorless solid. | CCOC(=O)N1CC[C@@H](NC(=O)c2c[nH]c3c(-c4c(OCC)ccc5c4OCO5)ncnc23)C1 | null | null | null |
414,032 | ord_dataset-275344fd078b4340b89ca0b6e92beb95 | null | 1998-01-01T00:10:00 | true | C([N:8]([C:23]([C:25]1([CH3:36])[C:30](=[O:31])[NH:29][C:28]2[CH:32]=[CH:33][CH:34]=[CH:35][C:27]=2[S:26]1)=[O:24])[C@H:9]([C:11]([NH:13][C@@H:14]([C:20](=[O:22])[NH2:21])[CH2:15][CH2:16][C:17]([O-:19])=[O:18])=[O:12])[CH3:10])C1C=CC=CC=1>CO.[Pd]>[CH3:36][C:25]1([C:23]([NH:8][C@H:9]([C:11]([NH:13][C@@H:14]([C:20](=[O:2... | C[C@@H](C(=O)N[C@H](CCC(=O)[O-])C(N)=O)N(Cc1ccccc1)C(=O)C1(C)Sc2ccccc2NC1=O | 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 | 12 | Benzyl-N-(3,4-dihydro-2-methyl-3-oxo-2H-1,4-benzothiazine-2-carbonyl)-L-alanyl-D-isoglutaminate (485 mg, 1.06 mmoles) was dissolved in methanol (17 ml), Pd/C (10%, 75 mg) was added thereto and it was hydrogenated at normal pressure for 12 hours. After the removal of the catalyst and evaporation of the solvent, there we... | C[C@H](NC(=O)C1(C)Sc2ccccc2NC1=O)C(=O)N[C@H](CCC(=O)O)C(N)=O | null | 59.2 | null |
351,121 | ord_dataset-127eb5fdd5b4402e92b51d0b55a5dcb5 | null | 1997-01-01T00:01:00 | true | [CH:1]1([C:4]2[N:8]([CH2:9][C:10]3[CH:15]=[CH:14][C:13]([C:16]4[C:17]([C:22]([O:24]C(C)(C)C)=[O:23])=[CH:18][CH:19]=[CH:20][CH:21]=4)=[CH:12][CH:11]=3)[C:7]3[CH:29]=[C:30]([C:34]4[N:35]=[C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][N:37]5[CH:42]=4)[CH:31]=[C:32]([CH3:33])[C:6]=3[N:5]=2)[CH2:3][CH2:2]1.FC(F)(F)C(O)=O>>[CH:1]1([... | Cc1cc(-c2cn3ccccc3n2)cc2c1nc(C1CC1)n2Cc1ccc(-c2ccccc2C(=O)OC(C)(C)C)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | Prepared analogously to Example 208 from tert.butyl 4'-[(2-cyclopropyl-4-methyl-6-(imidazo[1,2-a]pyridin-2-yl)-benzimidazol-1-yl)-methyl]-biphenyl-2-carboxylate and trifluoroacetic acid. | Cc1cc(-c2cn3ccccc3n2)cc2c1nc(C1CC1)n2Cc1ccc(-c2ccccc2C(=O)O)cc1 | null | null | null |
908,245 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | I[C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][C:10]([CH3:14])([OH:13])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][C:27]([NH:30][C:31](=[O:34])[C:32]#[CH:33])=[CH:26][CH:25]=2)=[CH:20][CH:19]=1>ClCCl.CO>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2[CH:29]=[CH:28][... | C#CC(=O)Nc1ccc(-c2ccc(Cl)cc2)cc1 | CC1(O)CCN(Cc2ccc(I)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 | Prepared analogously to Example 1.1.d. from 1-(4-iodobenzyl)-4-methylpiperidin-4-ol and propynoic acid-(4′-chlorobiphenyl-4-yl)amide. Yield: 25 mg (13% of theory); melting point: 192° C.-193° C.; C28H27ClN2O2 (M=458.99); calc.: molecular ion peak (M+H)+: 459/461; found: molecular ion peak (M+H)+: 459/461; Rf value: 0.2... | CC1(O)CCN(Cc2ccc(C#CC(=O)Nc3ccc(-c4ccc(Cl)cc4)cc3)cc2)CC1 | null | null | null |
216,310 | ord_dataset-67ed03c283094854909157b1038e38e3 | null | 1990-01-01T00:10:00 | true | C([O:4][C:5]1[CH:31]=[CH:30][C:8]([C:9]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][C:14]([O:24]C(=O)C)=[CH:15][C:16]=3[O:20]C(=O)C)[O:11][C:10]=2[CH2:28][Br:29])=[CH:7][CH:6]=1)(=O)C.Br>>[OH:4][C:5]1[CH:31]=[CH:30][C:8]([C:9]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][C:14]([OH:24])=[CH:15][C:16]=3[OH:20])[O:11][C:10]=2[CH2:28][... | CC(=O)Oc1ccc(-c2c(CBr)oc3cc(OC(C)=O)cc(OC(C)=O)c3c2=O)cc1 | null | null | Br | 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 | 100 | null | A mixture of 4',5,7-triacetoxy-2-bromomethylisoflavone (1 g) and 48% hydrobromic acid (7 ml) was heated at 100° C. for one hour, the reaction mixture was cooled with stirring, and the solid which separated out was collected by filtration and washed with water, giving 0.7 g of 4',5,7-trihydroxy-2-bromomethylisoflavone. | O=c1c(-c2ccc(O)cc2)c(CBr)oc2cc(O)cc(O)c12 | null | 94.3 | null |
1,240,182 | ord_dataset-e96f5a2842f14e5380461c234100f05a | null | 2012-01-01T00:12:00 | true | Br[C:2]1[S:3][C:4]([C:7](=[O:10])[CH2:8][CH3:9])=[CH:5][N:6]=1.[CH3:11][S:12]([O-])(=[O:14])=[O:13].[Na+]>CS(C)=O.CCOC(C)=O.[Cu]I>[CH3:11][S:12]([C:2]1[S:3][C:4]([C:7](=[O:10])[CH2:8][CH3:9])=[CH:5][N:6]=1)(=[O:14])=[O:13] | CCC(=O)c1cnc(Br)s1 | CS(=O)(=O)[O-] | null | [Cu]I | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 120 | null | To a solution of 1-(2-bromo-thiazol-5-yl)-propan-1-one (75 mg, 0.34 mmol) in dimethyl sulfoxide (3 mL) was added the sodium methanesulfonate (41 mg, 0.34 mmol) followed by copper (I) iodide (65 mg, 0.34 mmol). The mixture was heated in a microwave at 120° C. for 1 hour. The reaction was diluted with EtOAc (20 mL) and w... | CCC(=O)c1cnc(S(C)(=O)=O)s1 | null | null | null |
694,853 | ord_dataset-a7baa616c65d42559e25ca0ba61e0744 | null | 2006-01-01T00:01:00 | true | [OH:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Br[C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1>CN(C)C=O.[Cu]>[N:27]1[CH:28]=[CH:29][CH:30]=[C:25]([O:1][C:2]2[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[C... | Brc1cccnc1 | O=C(OCc1ccccc1)c1ccc(O)cc1 | null | [Cu] | CC(C)(C)[O-] | [K+] | 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 | 1 | To a solution of benzyl 4-hydroxybenzoate (25.0 g, 110 mmol) in N,N-dimethylformamide (60 ml) was added potassium tert-butoxide (12.3 g, 110 mmol), and the mixture was stirred at room temperature for 1 hr. The reaction solution was evaporated under reduced pressure, and 3-bromopyridine (25.0 g, 110 mmol), a copper powd... | O=C(OCc1ccccc1)c1ccc(Oc2cccnc2)cc1 | null | null | null |
482,390 | ord_dataset-cb5c1a9eddff4790b1bd650617c32d34 | null | 2000-01-01T00:11:00 | true | [OH:1][C:2]1[CH:21]=[CH:20][C:5]2[C:6](=[O:19])[C:7](=[CH:9][C:10]3[CH:18]=[CH:17][C:16]4[O:15][CH2:14][O:13][C:12]=4[CH:11]=3)[O:8][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[CH2:33](I)[CH3:34]>C(OCC)(=O)C>[CH2:33]([O:1][C:2]1[CH:21]=[CH:20][C:5]2[C:6](=[O:19])[C:7](=[CH:9][C:10]3[CH:18]=[CH:17][C:16]4[O:15][C... | CCI | O=C1C(=Cc2ccc3c(c2)OCO3)Oc2cc(O)ccc21 | 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 | 25 | null | After 6-hydroxy-2-piperonylidene-3(2H)-benzofuranone 1 g and potassium carbonate 1.95 g were added to dimethylformamide 10 ml, ethyl iodide 0.48 ml was added, and the mixture was reacted at a temperature of 100° C. for two hours. After the solution was cooled to room temperature, ethyl acetate 200 ml was added. The eth... | CCOc1ccc2c(c1)OC(=Cc1ccc3c(c1)OCO3)C2=O | null | null | null |
1,014,451 | ord_dataset-f024e9664ab64906a71a2ff6004cb3d0 | null | 2010-01-01T00:12:00 | true | [NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=2[C:12]([O-:14])=[O:13])=O)=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20].[BH4-].[Na+]>C1COCC1.CO>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:10]3[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=3[C:12](=[O:14])[O:13]2)=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20] | Nc1ccc(C(=O)c2ccccc2C(=O)[O-])cc1[N+](=O)[O-] | null | null | [BH4-] | [Na+] | 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 | 0.67 | To a solution of 2-[(4-amino-3-nitrophenyl)carbonyl]benzoate (8.36 g, 27.8 mmol) in THF (100 mL) and methanol (30 mL) at 0° C. was added sodium borohydride (3.0 g, 79 mmol). The mixture was stirred for 40 min, and then unreacted hydride was quenched with 10% aqueous citric acid. The organic solvents were removed in vac... | Nc1ccc(C2OC(=O)c3ccccc32)cc1[N+](=O)[O-] | null | null | null |
1,486,622 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | Br[C:2]1[CH:3]=[C:4]([N:8]2[CH2:16][CH:15]3[CH2:17][N:11]4[CH2:12][CH:13]([CH2:18][CH:9]2[CH2:10]4)[CH2:14]3)[CH:5]=[N:6][CH:7]=1.[N:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1>>[N:6]1[CH:5]=[C:4]([N:8]2[CH2:16][CH:15]3[CH2:17][N:11]4[CH2:12][CH:13]([CH2:18][CH:9]2[CH2:10]4)[CH2:14]3)[CH:3]=[C:2]([C:22]2[CH:23]=[... | OB(O)c1ccncc1 | Brc1cncc(N2CC3CC4CC2CN(C4)C3)c1 | 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 the product of Example 65A and 4-pyridinylboronic acid according to General Method B: LC-MS Method B (ESI+) m/z 307.0 (M+H)+, retention time 1.54 minutes. | c1cc(-c2cncc(N3CC4CC5CC3CN(C5)C4)c2)ccn1 | null | null | null |
866,210 | ord_dataset-b8b98725045d45bdbd73512048f4b47e | null | 2009-01-01T00:02:00 | true | [Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:31])[C:10]3([CH:15]([C:16]4[CH:21]=[C:20]([C:22](O)=[O:23])[CH:19]=[C:18]([Cl:25])[CH:17]=4)[CH2:14][C:13](=[O:26])[NH:12][CH:11]3[C:27](=[CH2:30])[CH2:28][CH3:29])[C:5]2=[CH:4][CH:3]=1.N1C(F)=NC(F)=NC=1[F:34].N1C=CC=CC=1>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:31])[C:10]... | C=C(CC)C1NC(=O)CC(c2cc(Cl)cc(C(=O)O)c2)C12C(=O)Nc1cc(Cl)ccc12 | Fc1nc(F)nc(F)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | ClCCl | null | null | null | null | null | null | null | null | null | 0 | 2 | To the solution of racemic (2′R,3R,4′S)-6-chloro-4′-(3-chloro-5-hydroxycarbonyl-phenyl)-2′-(1-methylene-propyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (0.2 g, 0.43 mmol) prepared in example 93 in dichloromethane (20 mL) at 0° C. was added cyanuric fluoride (48 mg, 0.35 mmol) (Alfa) and pyridine (37 mg, 0.48 mmo... | C=C(CC)C1NC(=O)CC(c2cc(Cl)cc(C(=O)F)c2)C12C(=O)Nc1cc(Cl)ccc12 | null | null | null |
1,039,573 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | [Br:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH:14]2[CH2:17][N:16]([C@@H:18]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=3)[C:19]3[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=3)[C:22]([OH:24])=[O:23])[CH2:15]2)[C:10]([F:13])([CH3:12])[CH3:11])[CH:5]=[C:6]([F:8])[CH:7]=1.Cl.[CH3:36][CH2:37]O>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([C@... | CCO | CC(C)(F)[C@H](c1cc(F)cc(Br)c1)C1CN([C@@H](c2ccc(Cl)cc2)c2cccc(C(=O)O)c2)C1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | null | To a mixture of 5.72 g (10.4 mmol) of 3-[(S)-{3-[(1S)-1-(3-bromo-5-fluorophenyl)-2-fluoro-2-methylpropyl]azetidin-1-yl}(4-chlorophenyl)methyl]benzoic acid in 230 mL of EtOH, was added a solution of 25 mL of 4N HCl in dioxane. After 7.5 h at reflux, the solution was cooled and concentrated to remove solvents. To the res... | CCOC(=O)c1cccc([C@H](c2ccc(Cl)cc2)N2CC([C@@H](c3cc(F)cc(Br)c3)C(C)(C)F)C2)c1 | null | null | null |
1,679,393 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | [Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([CH3:10])[CH:3]=1.O[N:12]=[C:13]([C:15]1[O:16][CH:17]=[CH:18][CH:19]=1)[NH2:14]>N1CCCCC1>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]2[O:7][N:12]=[C:13]([C:15]3[O:16][CH:17]=[CH:18][CH:19]=3)[NH:14]2)=[C:4]([CH3:10])[CH:3]=1 | Cc1cc(Cl)ccc1C=O | NC(=NO)c1ccco1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCNCC1 | null | null | null | null | null | null | null | null | null | null | 100 | null | A mixture of 4-chloro-2-methylbenzaldehyde (229 mg, 1.49 mmol), N′-hydroxyfuran-2-carboximidamide (263 mg, 2.1 mmol) and one drop of piperidine was heated to 100° C. for 4 h. It was cooled to RT and purified by automated column chromatography on the ISCO-companion (SiO2, gradient heptane/ethyl acetate) to give the 5-(4... | Cc1cc(Cl)ccc1C1NC(c2ccco2)=NO1 | null | 24.2 | null |
479,035 | ord_dataset-21c1b1c06c7e4e09a38b5b1c71a32e52 | null | 2000-01-01T00:10:00 | true | [F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]1[CH2:12][CH2:13][N:14]([CH3:17])[CH2:15][CH:16]=1.[N+:18]([C:21]1[CH:22]=[C:23]([S:27](Cl)(=[O:29])=[O:28])[CH:24]=[CH:25][CH:26]=1)([O-:20])=[O:19]>>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:27]([C:23]1[CH:24]=[CH:25][CH:26]=[C:21](... | CN1CC=C(c2c[nH]c3ccc(F)cc23)CC1 | O=[N+]([O-])c1cccc(S(=O)(=O)Cl)c1 | 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 | (31.0 mg, 56%), from 5-fluoro-3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (Example 4b, 30.1 mg, 0.131 mmol) and 3-nitrophenylsulfonyl chloride (58.1 mg, 0.26 mmol); HRMS-FAB+ for C20H19N3O4SF calculated MH+ : 416.10803; found: 416.10631. | CN1CC=C(c2cn(S(=O)(=O)c3cccc([N+](=O)[O-])c3)c3ccc(F)cc23)CC1 | null | null | null |
919,715 | ord_dataset-8e59bd24817446f7b1c68e805b8e5f1d | null | 2009-01-01T00:11:00 | true | [C:1]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:16][CH2:15][C:14]([F:18])([F:17])[CH2:13][CH2:12]2)[C:8]2[CH:19]=[CH:20][C:21]([S:23](Cl)(=[O:25])=[O:24])=[CH:22][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.[C:36]([O:40][C:41]([NH:43][C@H:44]1[CH2:48][CH2:47][NH:46][CH2:45]1)=[O:42])([CH3:39])([CH3:38])[CH3:37]>C(... | CC(C)(C)OC(=O)N[C@H]1CCNC1 | CC(C)(C)c1nc2cc(S(=O)(=O)Cl)ccc2n1CC1CCC(F)(F)CC1 | 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 | null | null | Following the same procedure in Example 1, step A, using 2-tert-butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazole-5-sulfonyl chloride (2 g, 5 mmol), N,N-diisopropylethylamine (3.5 mL, 20 mmol) and (3S)-(−)-3-(tert-butoxycarbonylamino)pyrrolidine (1.4 g, 7.5 mmol) in (10 mL) methylene chloride. The crude product... | CC(C)(C)OC(=O)N[C@H]1CCN(S(=O)(=O)c2ccc3c(c2)nc(C(C)(C)C)n3CC2CCC(F)(F)CC2)C1 | null | null | null |
1,062,050 | ord_dataset-ffbef48837674f39816de887b5dc8bae | null | 2011-01-01T00:06:00 | true | CO[N:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=2[O:18][CH3:19])=[C:7]([O:20][CH3:21])[CH:6]=1>[Pd].C(O)C.Cl>[F:17][C:15]1[CH:14]=[CH:13][C:12]([O:18][CH3:19])=[C:11]([C:8]2[CH:9]=[CH:10][C:5]([CH2:4][NH2:3])=[CH:6][C:7]=2[O:20][CH3:21])[CH:16]=1 | CON=Cc1ccc(-c2cc(F)ccc2OC)c(OC)c1 | null | null | [Pd] | Cl | 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 | To a stirred solution of 4-hydroxy-3-methoxybenzaldehyde (2 g, 14.7 mmol) in dichloromethane (20 ml) was slowly added trifluoromethanesulfonic anhydride (4.5 g, 17.64 mmol) and pyridine (1.5 ml, 14.7 mmol) at 0° C. under nitrogen atmosphere. The solution was stirred for 16 h at ambient temperature, ice-water slurry add... | COc1cc(CN)ccc1-c1cc(F)ccc1OC | null | 164 | null |
25,538 | ord_dataset-2ada3fda46fc44719ba0c8001f53c1b3 | null | 1977-01-01T00:06:00 | true | [CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N:8]([C:17]([N:21]=[C:22]=[O:23])([CH2:19][CH3:20])[CH3:18])=[N:9][C:10]([N:14]=[C:15]=[O:16])([CH2:12][CH3:13])[CH3:11]>CCCCC>[N:8]([C:17]([NH:21][C:22]([NH:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:23])([CH2:19][CH3:20])[CH3:18])=[N:9][C:10]([NH:14][C:15](... | CCC(C)(N=C=O)N=NC(C)(CC)N=C=O | NC1CCCCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCC | null | null | null | null | null | null | null | null | null | null | 25 | 1 | To a stirred solution of 4.7 grams (0.0474 moles) of cyclohexylamine in 30 ml of pentane in a 50 ml erlenmeyer flask cooled in a water bath was added 5.32 grams (0.0237 moles) of 2,2'-azobis(2-isocyanatobutane) (from Example XXXVI) dropwise over 20 minutes while holding the reaction temperature below 30° C. After the a... | CCC(C)(N=NC(C)(CC)NC(=O)NC1CCCCC1)NC(=O)NC1CCCCC1 | null | null | null |
701,016 | ord_dataset-bbd7e53f000345838ad4920a07a169ff | null | 2006-01-01T00:03:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:16]([NH2:26])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].C(N(CC)C(C)C)(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[CH2:16]([NH:26][C:10](=[O:1... | CC(C)(C)OC(=O)N1CCC[C@H]1C(=O)O | CCCCCCCCCCN | null | F[P-](F)(F)(F)(F)F | c1ccc2c(c1)nnn2O[P+](N1CCCC1)(N1CCCC1)N1CCCC1 | 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 | 42 | N-(tert-butoxycarbonyl)-L-proline (Aldrich Chemical Company, Milwaukee, Wis.) (137 mg; 0.64 mmol) is dissolved in methylene chloride (3 mL) at ambient temperature. n-Decylamine (120 mg; 0.76 mmol), N,N-diisopropylethylamine (181 mg; 1.40 mmol) and PyBOP (397 mg; 0.76 mmol) are added sequentially. The reaction is stirre... | CCCCCCCCCCNC(=O)[C@@H]1CCCN1C(=O)OC(C)(C)C | null | null | null |
1,339,275 | ord_dataset-08852243bba44cb28769a5833f1515fe | null | 2013-01-01T00:09:00 | true | O=P(Cl)(Cl)Cl.[CH:6]([C:9]1[NH:19][C:12]2=[CH:13][N:14]=[C:15]([O:17][CH3:18])[CH:16]=[C:11]2[CH:10]=1)([CH3:8])[CH3:7].CN([CH:23]=[O:24])C>>[CH:6]([C:9]1[NH:19][C:12]2=[CH:13][N:14]=[C:15]([O:17][CH3:18])[CH:16]=[C:11]2[C:10]=1[CH:23]=[O:24])([CH3:8])[CH3:7] | CN(C)C=O | COc1cc2cc(C(C)C)[nH]c2cn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=P(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 90 | 0.5 | POCl3 (1.1 ml, 12.5 mmol) was added to anhydrous DMF (10 ml) at 0° C. slowly and stirred for 0.5 h. This was added to a solution of 2-isopropyl-5-methoxy-1H-pyrrolo[2,3-c]pyridine (Compound 5, 468 mg, 2.5 mmol) in anhydrous DMF (15 ml) at room temperature. The mixture was then heated to 90° C. for 2 h and cooled to roo... | COc1cc2c(C=O)c(C(C)C)[nH]c2cn1 | null | null | null |
785,230 | ord_dataset-4ad5db8537994579bef51f16dd8bf0bd | null | 2007-01-01T00:08:00 | true | C([O:3][C:4](=[O:45])[CH:5]([O:7][P:8]([CH2:17][CH2:18][NH:19][C:20]([C:22]1[C:23]2[CH:24]=[CH:25][CH:26]=[N:27][C:28]=2[C:29]([OH:44])=[C:30]2[C:34](=[O:35])[N:33]([CH2:36][C:37]3[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=3)[CH2:32][C:31]=12)=[O:21])([O:10]C1C=CC=CC=1)=[O:9])[CH3:6])C.O.[OH-].[Na+]>C(#N)C>[F:43][C:4... | CCOC(=O)C(C)OP(=O)(CCNC(=O)c1c2c(c(O)c3ncccc13)C(=O)N(Cc1ccc(F)cc1)C2)Oc1ccccc1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | O | null | null | null | null | null | null | null | null | null | 25 | 3 | To 2-[(2-{[7-(4-fluoro-benzyl)-9-hydroxy-8-oxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinoline-5-carbonyl]-amino}-ethyl)-phenoxy-phosphinoyloxy]-propionic acid ethyl ester 221 (15 mg, 0.024 mmol) dissolved in acetonitrile (0.10 ml) and water (0.05 ml) was added 1.0 M NaOH (0.072 ml). The reaction mixture was stirred at room tem... | CC(OP(=O)(O)CCNC(=O)c1c2c(c(O)c3ncccc13)C(=O)N(Cc1ccc(F)cc1)C2)C(=O)O | null | 58.3 | null |
401,409 | ord_dataset-7fed188163cf4ccca934ec71504c7f8a | null | 1998-01-01T00:05:00 | true | [CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26](Cl)=[O:27]>C1(C)C=CC=CC=1>[Cl:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26]([O:14][CH:11]1[CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:3]=... | OC1CCN(Cc2ccccc2)CC1 | O=C(Cl)c1cccc(Cl)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | 0.5 g (0.0026 mol) of 1-benzyl-4-hydroxypiperidine and 0.64 ml (0.0046 mol) of triethylamine were dissolved in 20 ml of toluene and treated with 0.27 ml (0.0021 mol) of 3-chloro-benzoyl chloride. The mixture was boiled at reflux for 6 hrs., the precipitate was filtered off and the filtrate was concentrated. The residue... | O=C(OC1CCN(Cc2ccccc2)CC1)c1cccc(Cl)c1 | null | 81.7 | null |
1,392,598 | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | null | 2014-01-01T00:02:00 | true | CC(C)([O-])C.[K+].O1CCCC1.[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][OH:18])=[CH:15][CH:14]=1.Cl[C:22]1[N:26]([CH3:27])[N:25]=[CH:24][C:23]=1[CH:28]=[O:29]>O>[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][O:18][C:22]2[N:26]([CH3:27])[N:25]=[CH:24][C:23]=2[CH:28]=[O:29])=[CH:15][CH:14]=1 | Cn1ncc(C=O)c1Cl | OCc1ccc(Cl)cc1 | null | CC(C)(C)[O-] | [K+] | 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 | 0.33 | Under cooling in an ice bath, potassium tert-butoxide (217 mg) was added to a tetrahydrofuran (2.8 mL) solution of 4-chlorobenzyl alcohol (217 mg), and the obtained solution was then stirred for 20 minutes. Under cooling in an ice bath, 5-chloro-1-methyl-1H-pyrazol-4-carbaldehyde (200 mg) was added to the reaction solu... | Cn1ncc(C=O)c1OCc1ccc(Cl)cc1 | null | 36.6 | null |
1,375,218 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | Br[C:2](Br)=[CH:3][CH:4]1[CH2:7][CH:6]([CH2:8][CH:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[CH2:5]1.C([Li])CCC.[Si:20]([O:37][CH2:38][CH2:39][CH:40]([C:49](=[O:54])NCOC)[CH2:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])([C:33]([CH3:36])([CH3:35])[CH3:34])([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1... | COCNC(=O)C(CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)CC(=O)OC(C)(C)C | CCC(CC)CC1CC(C=C(Br)Br)C1 | null | [Cl-] | [Li]CCCC | [NH4+] | 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 | 1-(2,2-Dibromovinyl)-3-(2-ethylbutyl)cyclobutane (9.78 g) and tetrahydrofuran (100 mL) were mixed. To the mixture was added dropwise n-butyllithium (1.65 M in hexane) (39 mL) at −78° C. The mixture was stirred under ambient temperature. To the mixture was added dropwise a solution of tert-butyl 5-(tert-butyldiphenylsil... | CCC(CC)CC1CC(C#CC(=O)C(CCO[Si](c2ccccc2)(c2ccccc2)C(C)(C)C)CC(=O)OC(C)(C)C)C1 | null | 75.8 | null |
136,981 | ord_dataset-a1d4c9f5edd844798727d514977ca73e | null | 1985-01-01T00:11:00 | true | [CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]([NH:16][CH2:17][CH2:18]Br)=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]([O-:28])(=[S:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[K+]>CC(C)=O>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]([NH:16][CH2:17][CH2:18][S:27][C:20](=[O:28])[C:21]1[CH:... | O=C(CCNC(=O)OCc1ccccc1)NCCBr | [O-]C(=S)c1ccccc1 | null | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | null | null | null | null | null | null | null | null | null | null | null | 1 | To the solution of 3-(benzyloxycarbonylamino)-N-(2-bromoethyl)propionamide (10.0 g, 0.03 mol) in acetone (250 ml), acetone (100 ml) solution of potassium thiobenzoate (5.35 g, 0.03 mol) is added. The mixture is stirred for 1 hour and insoluble substance is filtered off. The filtrate is concentrated in vacuo and the res... | O=C(CCNC(=O)OCc1ccccc1)NCCSC(=O)c1ccccc1 | null | 68.1 | null |
402,438 | ord_dataset-7fed188163cf4ccca934ec71504c7f8a | null | 1998-01-01T00:05:00 | true | C([O:8][C:9]1[CH:26]=[CH:25][C:12]([C:13]([N:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:17][CH2:16]2)=[O:14])=[CH:11][C:10]=1[CH2:27][CH:28]([CH3:30])[CH3:29])C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[OH:8][C:9]1[CH:26]=[CH:25][C:12]([C:13]([N:15]2[CH2:16][CH2:17][N:18]([CH2:21][CH:22]([CH3:24])[CH3:23])[CH... | [H][H] | CC(C)Cc1cc(C(=O)N2CCN(CC(C)C)CC2)ccc1OCc1ccccc1 | 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 | 1-(4-benzyloxy-3-isobutylbenzoyl)-4-isobutylpiperazine (6.78 g) was dissolved in ethanol (250 ml) and then, with 10% palladium charcoal (0.14 g) added thereto, the mixture was stirred at room temperature for 24 hours in a hydrogen gas atmosphere. After the reaction mixture was filtered under a suction, the filtrate was... | CC(C)Cc1cc(C(=O)N2CCN(CC(C)C)CC2)ccc1O | null | 89.5 | null |
1,666,286 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[C:11]2[CH:12]=[N:13][C:14]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[N:15][CH:16]=2)=[CH:9]\[CH3:10])=[CH:4][CH:3]=1.[H][H]>CO.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:11]2[CH:12]=[N:13][C:14]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[N:15][CH:16]=2)[CH2:9][CH3... | [H][H] | C/C=C(\c1ccc(F)cc1)c1cnc(N2CCNCC2)nc1 | 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 | 25 | 1 | To a solution of (E)-5-(1-(4-fluorophenyl)prop-1-enyl)-2-(piperazin-1-yl)pyrimidine (170 mg, 0.57 mmol) in methanol (10 mL) was added Pd/C (30 mg). The mixture was exposed to 1 atm hydrogen (balloon) and stirred at RT for 1 h. The mixture was filtrated, and the filtrate was concentrated to an oil, which was purified by... | CCC(c1ccc(F)cc1)c1cnc(N2CCNCC2)nc1 | null | 52.6 | null |
738,084 | ord_dataset-76dd1b78ee414d2da0ed30700ef026f7 | null | 2006-01-01T00:10:00 | true | [CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([O:10]C)=[CH:6][C:4]=1[NH2:5].[Cl:12][C:13]1[CH:21]=[C:20]([O:22]C)[CH:19]=[CH:18][C:14]=1C(O)=O>>[Cl:12][C:13]1[CH:21]=[C:20]([OH:22])[CH:19]=[CH:18][C:14]=1[C:1]1[O:2][C:3]2[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:4]=2[N:5]=1 | COc1ccc(OC)c(N)c1 | COc1ccc(C(=O)O)c(Cl)c1 | 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 in substantially the same manner as described in Example 1, from 2,5-dimethoxyaniline, and 2-chloro-4-methoxybenzoic acid and was obtained as a white solid, m.p. 253–255° C.; MS m/e 262 (M+H)+. | Oc1ccc(-c2nc3cc(O)ccc3o2)c(Cl)c1 | null | null | null |
369 | ord_dataset-a0eff6fe4b4143f284f0fc5ac503acad | null | 1976-01-01T00:01:00 | true | C([Li])CCC.[CH3:6][P:7](=[O:12])([O:10][CH3:11])[O:8][CH3:9].[NH:13]1[C:21]2[C:16](=[CH:17][C:18]([O:22][CH2:23][C:24](OCC)=[O:25])=[CH:19][CH:20]=2)[CH:15]=[CH:14]1.Cl>CCCCCC.O1CCCC1>[O:25]=[C:24]([CH2:23][O:22][C:18]1[CH:17]=[C:16]2[C:21](=[CH:20][CH:19]=1)[NH:13][CH:14]=[CH:15]2)[CH2:6][P:7](=[O:12])([O:10][CH3:11])... | CCOC(=O)COc1ccc2[nH]ccc2c1 | COP(C)(=O)OC | null | Cl | [Li]CCCC | null | 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 | n-Butyl-lithium (21.8ml. of a 2.92M solution in hexane) was added to a solution of dimethyl methylphosphonate (6.2g.) in dry tetrahydrofuran (50ml.) at -78°C. in an atmosphere of argon. After 10 minutes, a solution of ethyl 5-indolyloxyacetate (5.5g.) in dry tetrahydrofuran (50ml.) was added dropwise, and the mixture w... | COP(=O)(CC(=O)COc1ccc2[nH]ccc2c1)OC | null | null | null |
1,745,675 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | [NH2:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:8].[C:16]([O:20][C:21]([NH:23][C@@H:24]([CH3:28])[C:25](O)=[O:26])=[O:22])([CH3:19])([CH3:18])[CH3:17].CCN=C=NCCCN(C)C.Cl>CN(C)C=O>[O:26]=[C:25]([NH:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](=[O:8])[NH:9][C:10]1[CH:15]=[... | C[C@H](NC(=O)OC(C)(C)C)C(=O)O | Nn1cccc1C(=O)Nc1ccccc1 | null | CCN=C=NCCCN(C)C | Cl | 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 | 2.00 g (9.94 mmol) of 1-amino-N-phenyl-1H-pyrrole-2-carboxamide were dissolved in 50 mL dimethylformamide. To this solution, 2.07 g (10.94 mmol) of (S)-2-(tert-butoxycarbonylamino)propanoic acid (purchased from Aldrich®, cat. no. 13,451-1) and 2.10 g (10.95 mmol) of EDC.HCl were added and the resulting reaction mixture... | C[C@H](NC(=O)OC(C)(C)C)C(=O)Nn1cccc1C(=O)Nc1ccccc1 | null | 59.7 | null |
55,439 | ord_dataset-159c363342e44b539e7a5975c873e30d | null | 1979-01-01T00:05:00 | true | [Br:1][C:2]1[C:3]([CH2:9]O)=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8].Cl.[NH2:12][CH2:13][CH2:14][SH:15]>Br>[BrH:1].[BrH:1].[Br:1][C:2]1[C:3]([CH2:9][S:15][CH2:14][CH2:13][NH2:12])=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8] | NCCS | Cc1ccnc(CO)c1Br | null | Br | 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 | A mixture of 3-bromo-2-hydroxymethyl-4-methylpyridine (5.8), cysteamine hydrochloride (3.5 g) and hydrobromic acid (48%, 50 ml) was refluxed for 6 hours and evaporated to dryness. The residue was crystallised from isopropanol/methanol to give 2-(3-bromo-4-methyl-2-pyridylmethylthio)ethylamine dihydrobromide (8.5 g) m.p... | Cc1ccnc(CSCCN)c1Br | null | null | null |
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