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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
412,991 | ord_dataset-fbdd058349aa456f812e3546c84baab5 | null | 1998-01-01T00:09:00 | true | [NH2:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][CH:7]([N:15]([CH3:17])[CH3:16])[CH2:6][C:5]2=1.[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>>[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([NH:1][C:2]2[CH:3]=[C:4]3[C:12](=[CH:13][CH:14]=2)[NH:11][C:10]2[C... | Cc1ccc(S(=O)(=O)Cl)cc1 | CN(C)C1CCc2[nH]c3ccc(N)cc3c2C1 | 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 | Beginning with 10.4 mg (0.046 mMol) 6-amino-3-(dimethyl)amino-1,2,3,4-tetrahydro-9H-carbazole and 12.8 mg (0.067 mMol) 4-methylbenzenesulfonyl chloride, 5.3 mg (31%) of the title compound were recovered as a light beige solid. | Cc1ccc(S(=O)(=O)Nc2ccc3[nH]c4c(c3c2)CC(N(C)C)CC4)cc1 | null | 30 | null |
784,363 | ord_dataset-4ad5db8537994579bef51f16dd8bf0bd | null | 2007-01-01T00:08:00 | true | [CH3:1][C@H:2]([C:15]([OH:17])=[O:16])[C:3]1[CH:8]=[CH:7][C:6]2[CH:9]=[C:10]([O:13][CH3:14])[CH:11]=[CH:12][C:5]=2[CH:4]=1.[F:18][C:19]([F:27])([C:23]([F:26])([F:25])[F:24])[CH:20](O)[CH3:21].C(Cl)CCl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:14][O:13][C:10]1[CH:9]=[C:6]2[C:5](=[CH:12][CH:11]=1)[CH:4]=[C:3]([CH:2]([CH3:1])[C:15]([... | CC(O)C(F)(F)C(F)(F)F | COc1ccc2cc([C@H](C)C(=O)O)ccc2c1 | null | CN(C)c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCCl | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 8 | A mixture of (S)-naproxen (9.23 g, 40.1 mmol), racemic 3,3,4,4,4-pentafluoro-2-butanol (6.58 g, 40.1 mmol), EDC (9.20 g, 48.0 mmol) and DMAP (4.89 g, 40.0 mmol) was dissolved in CH2Cl2 (40 mL) at room temperature. After stirring for 8 h at room temperature, the mixture was diluted with CH2Cl2, then washed successively ... | COc1ccc2cc(C(C)C(=O)O[C@@H](C)C(F)(F)C(F)(F)F)ccc2c1 | null | null | null |
653,921 | ord_dataset-fe016e2f90e741a590ad77fd5933161f | null | 2004-01-01T00:11:00 | true | [CH2:1]([NH2:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1([C:28](Cl)=[O:29])[C:27]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:21]2[C:16]1=[CH:17][CH:18]=[CH:19][CH:20]=2>>[CH2:1]([NH:9][C:28]([C:15]1([CH2:14][CH2:13][CH2:12][CH2:11][Br:10])[C:27]2[CH:26]=[CH:25][CH:24]... | NCCc1ccccc1 | O=C(Cl)C1(CCCCBr)c2ccccc2-c2ccccc21 | 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 | Prepared analogously to Example 1 from phenethylamine and 9-(4-bromo-butyl)-9H-fluorene-9-carboxylic acid chloride. | O=C(NCCc1ccccc1)C1(CCCCBr)c2ccccc2-c2ccccc21 | null | null | null |
111,905 | ord_dataset-5237a168f9214b7ca3db5a1dc3e62d07 | null | 1983-01-01T00:12:00 | true | C([O:8][P:9]1[O:14][CH2:13][C:12]([CH3:16])([CH3:15])[CH2:11][O:10]1)C1C=CC=CC=1.[CH2:17](I)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1(C)C(C)=CC=CC=1>[CH2:17]([P:9]1(=[O:8])[O:10][CH2:11][C:12]([CH3:15])([CH3:16])[CH2:13][O:14]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1 | ICc1ccccc1 | CC1(C)COP(OCc2ccccc2)OC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1C | null | null | null | null | null | null | null | null | null | null | null | 1.5 | A mixture of 2-benzyloxy-5,5-dimethyl-1,3,2-dioxaphosphorinane (100 g, 0.416 M) from Example II, benzyl iodide (1.0 g), and xylene (50 ml) was heated until the temperature reached 165° C., and then slowly dropped to 155° C. After 1.5 hrs, the mixture was allowed to cool to yield 92.4 g (92.4% yield) of pure crystalline... | CC1(C)COP(=O)(Cc2ccccc2)OC1 | null | 8,386.1 | null |
946,144 | ord_dataset-ed680843f6d14f5c9901869b2a06b4a4 | null | 2010-01-01T00:03:00 | true | [NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[C:9](N1C=CN=C1)(N1C=CN=C1)=[O:10].Cl>C1COCC1>[S:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH:1][C:9]1=[O:10] | O=C(n1ccnc1)n1ccnc1 | Nc1ccccc1S | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 12 | To 2-amino-benzenethiol (10 g, 79.9 mmol) in THF (200 mL) at room temperature was added carbonyldiimidazole (14.3 g, 87.9 mmol) and the reaction solution stirred for 12 hours. Upon disappearance of starting material, the reaction solution was poured into 1N HCl (125 mL) and extracted with ethyl acetate (125 mL). The or... | O=c1[nH]c2ccccc2s1 | null | null | null |
312,711 | ord_dataset-abe42048f0b84fa88446cee56a31e967 | null | 1995-01-01T00:07:00 | true | [NH3:1].[CH3:2][S:3]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13](Cl)(=[O:15])=[O:14])(=[O:5])=[O:4]>O1CCCC1>[CH3:2][S:3]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13]([NH2:1])(=[O:15])=[O:14])(=[O:5])=[O:4] | CS(=O)(=O)Oc1ccccc1S(=O)(=O)Cl | N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | Ammonia was passed at -30° C. into a solution of 130.3 g of 2-chlorosulfonylphenyl methanesulfonate in 1 l of tetrahydrofuran, and the conversion was checked by thin-layer chromatography. After the reaction was complete, the tetrahydrofuran was distilled off under reduced pressure from a water pump and the residue was ... | CS(=O)(=O)Oc1ccccc1S(N)(=O)=O | null | null | null |
815,181 | ord_dataset-50f99930fc41474db226bc80774b38df | null | 2008-01-01T00:04:00 | true | [CH2:1]([N:3]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[F:34])[C:4](=[O:26])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][S:15][C:16]2[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=2[C:18]([O:20]C)=[O:19])=[CH:9][CH:8]=1)[CH3:2].O.[OH-].[Li+]>C1COCC1>[CH2:1]([N:3]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:... | CCN(Cc1ccccc1F)C(=O)COc1ccc(CCSc2ccccc2C(=O)OC)cc1 | null | null | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | O | null | null | null | null | null | null | null | null | null | null | null | Methyl 2-{[2-(4-{2-[ethyl(2-fluorobenzyl)amino]-2-oxoethoxy}phenyl)ethyl]thio}-benzoate was dissolved in a mixture of THF (freshly distilled)/water (2/1, 3 ml), Lithium hydroxide (0.015 g, 0.629 mmol) was added. The reaction was performed in a single node microwave oven (5 min, 150 deg). THF was removed by evaporation.... | CCN(Cc1ccccc1F)C(=O)COc1ccc(CCSc2ccccc2C(=O)O)cc1 | null | 96.9 | null |
614,184 | ord_dataset-31fc6d0085ca4d8dbbcd3a5fa9dcedfb | null | 2003-01-01T00:11:00 | true | [Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH:4]=[CH:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12]C)=[O:11])=[CH:8][CH:7]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH:4]=[CH:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1 | COC(=O)c1ccc(C=Cc2ccccc2Cl)cc1 | 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 | 25 | 3 | A mixture of methyl 4-(2-chlorostyryl)benzoate (trans form) (1.42 g), 5N sodium hydroxide (1.6 ml) and methanol (20 ml) is stirred at room temperature for three hours, and refluxed for two hours. The mixture is evaporated to remove the methanol, and to the residue is added water. The mixture is acidified with conc. hyd... | O=C(O)c1ccc(C=Cc2ccccc2Cl)cc1 | null | 101 | null |
1,531,889 | ord_dataset-8d5c200bca27407ab9febe7598e16458 | null | 2015-01-01T00:01:00 | true | [C:1]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:6]=[CH:5][C:4]([C:7]2([C:10]3[N:14]4[CH2:15][CH2:16][S:17][C:18]([CH2:21][O:22][Si](C(C)(C)C)(C)C)([CH3:20])[CH2:19][C:13]4=[N:12][N:11]=3)[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.Cl>CO>[C:1]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:2]=[CH:3][C:4]([C:7]2([C:10... | CC1(CO[Si](C)(C)C(C)(C)C)Cc2nnc(C3(c4ccc(-c5ccccc5)cc4)CC3)n2CCS1 | null | null | Cl | 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 solution of the compound (197 mg, 0.39 mmol) obtained in Example 1-3) and 4 M hydrochloric acid (1,4-dioxane solution, 0.5 mL) in methanol (2 mL) was stirred at room temperature for 21 h. The reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogencarbonate was added to the residue,... | CC1(CO)Cc2nnc(C3(c4ccc(-c5ccccc5)cc4)CC3)n2CCS1 | null | 90.4 | null |
1,670,704 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [C:1]([C:3]12[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][C:5]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])([CH2:6]3)[CH2:4]1)[CH2:10]2)#[CH:2].Cl[C:22]1[CH:27]=[N:26][CH:25]=[CH:24][N:23]=1>C(#N)C.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2... | C#CC12CC3CC(C1)CC(NC(=O)OC(C)(C)C)(C3)C2 | Clc1cnccn1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 70 | 3 | To a stirred solution of tert-butyl 3-ethynyl-1-adamantylcarbamate (120 mg, 0.44 mmol) and 2-chloropyrazine (120 mg, 1.05 mmol) in TEA (3 mL) and acetonitrile (15 mL) was added Pd(PPh3)4 (5 mg, 0.04 mmol), followed by an addition of Cut (5 mg, 0.026 mmol) under N2 atmosphere. After stirring at 70° C. for three hours, t... | CC(C)(C)OC(=O)NC12CC3CC(CC(C#Cc4cnccn4)(C3)C1)C2 | null | 69.4 | null |
534,659 | ord_dataset-b1a34bc8c1204d51a772ed27396c794e | null | 2002-01-01T00:02:00 | true | [CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:17][C:16]2[NH:15][N:14]=[C:13]([CH3:18])[C:12]=2[C:11](=O)[CH2:10]1.[C:20]([NH:23][NH2:24])([NH2:22])=[NH:21].[ClH:25].Cl.O>C(O)C>[ClH:25].[NH:23]([N:24]=[C:11]1[CH2:10][CH:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[CH2:17][C:16]2[NH:15][N:14]=... | N=C(N)NN | COc1ccccc1C1CC(=O)c2c(C)n[nH]c2C1 | 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 6-(2-methoxyphenyl)-3-methyl-4,5,6,7-tetrahydroindazol-4-one (0.2 g), aminoguanidine hydrochloride (0.095 g), concentrated hydrochloric acid (0.12 ml), water (0.12 ml) and ethanol (30 ml) was refluxed for 1 hour. Under reduced pressure, the solvent was evaporated, and to the residue was added water. The mi... | COc1ccccc1C1CC(=NNC(=N)N)c2c(C)n[nH]c2C1 | null | 110.2 | null |
256,771 | ord_dataset-30ad5cf6083a45a387b45bebad1a4d65 | null | 1992-01-01T00:10:00 | true | [CH3:1][C:2]1[N:7]2[C:8](=[O:15])[C:9]([C:12]([OH:14])=O)=[CH:10][N:11]=[C:6]2[CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OCC)=O.[C:29]([NH2:34])([CH2:32][CH3:33])([CH3:31])[CH3:30]>C(Cl)(Cl)Cl>[C:29]([NH:34][C:12]([C:9]1[C:8](=[O:15])[N:7]2[C:2]([CH3:1])=[CH:3][CH:4]=[CH:5][C:6]2=[N:11][CH:10]=1)=[O:14])([CH2:32][CH3:33])([... | Cc1cccc2ncc(C(=O)O)c(=O)n12 | CCC(C)(C)N | null | CCOC(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | 0.08 | A mixture containing 8.16 g (0.04 mol) of 6-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid and 6.2 ml (0.044 mol) of triethylamine in 240 ml of chloroform is cooled below -10° C. by ice-salt. A solution of 4 ml (0.042 mol) of ethyl chloroformate in 20 ml of chloroform is dropped to the above mixture at a tem... | CCC(C)(C)NC(=O)c1cnc2cccc(C)n2c1=O | null | 54 | null |
118,105 | ord_dataset-3708161f4ba04e959b9a7a8d59fd86e1 | null | 1984-01-01T00:05:00 | true | Cl[C:2]([CH3:7])([OH:6])[C:3]([OH:5])=[O:4].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1.Cl>[OH-].[Na+]>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:7][CH:2]([OH:6])[C:3]([OH:5])=[O:4])=[CH:11][CH:10]=1 | Oc1ccc(Cl)cc1 | CC(O)(Cl)C(=O)O | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 25 | null | A mixture of 1.8 g (14.7 mmoles) 3=chlorolactic acid and 3.4 g p-chlorophenol in 15 ml 3.3 N sodium hydroxide was stirred under reflux for two hours. The mixture was cooled to room temperature and acidified to pH=3, with concentrated hydrochloric acid. The resulting white crystals were filtered and dissolved in hot wat... | O=C(O)C(O)COc1ccc(Cl)cc1 | null | null | null |
926,431 | ord_dataset-cc0899cd744f4f7f8e7f2463560faad1 | null | 2009-01-01T00:12:00 | true | [Cl:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]([N:13]2[CH2:19][CH2:18][C:17](=[O:20])[N:16]([CH2:21][CH2:22][CH2:23]OS(C)(=O)=O)[CH2:15][CH2:14]2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[I-:29].[Na+]>CC(=O)CC>[Cl:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]([N:13]2[CH2:19][CH2:18][C:17](=[O:20])[N:16]([CH2:21][CH2:22][CH2:2... | [I-] | CS(=O)(=O)OCCCN1CCN(C(=O)/C=C/c2ccc(Cl)c(Cl)c2)CCC1=O | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCC(C)=O | null | null | null | null | null | null | null | null | null | null | 95 | 0.5 | A solution of 0.50 g (1.11 mmol) of crude methanesulfonic acid 3-{4-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-propyl ester in 20 ml of 2-butanone was treated with 0.33 g (2.23 mmol) of sodium iodide and stirred at 95° C. for 30 min. The reaction was cooled, evaporated, suspended in 60 ml dichloro... | O=C(/C=C/c1ccc(Cl)c(Cl)c1)N1CCC(=O)N(CCCI)CC1 | null | null | null |
1,147,634 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | C([O:3][C:4](=[O:28])[CH2:5][N:6]1[C:10]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([F:19])[CH:13]=2)([CH3:11])[C:9](=[O:20])[N:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[C:7]1=[O:27])C.[OH-].[Na+]>C1COCC1.CS(C)=O>[F:18][C:16]1[CH:17]=[C:12]([C:10]2([CH3:11])[N:6]([CH2:5][C:4]([OH:28])=[O:3])[C:7](=[O:27])[N:8]... | CCOC(=O)CN1C(=O)N(c2ccccn2)C(=O)C1(C)c1cc(F)cc(F)c1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CS(C)=O | null | null | null | null | null | null | null | null | null | null | 16 | To a stirred solution of ethyl[5-(3,5-difluorophenyl)-5-methyl-2,4-dioxo-3-pyridin-2-ylimidazolidin-1-yl]acetate, isomer A from Step A (67.0 mg, 0.172 mmol) in THF (2 mL) was added a solution of 1 N NaOH (0.516 mL, 0.516 mmol) and stirring continued for 16 h. The reaction mixture was diluted with DMSO (1 mL) and purifi... | CC1(c2cc(F)cc(F)c2)C(=O)N(c2ccccn2)C(=O)N1CC(=O)O | null | null | null |
1,592,273 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [CH2:1]([NH:8][C:9]1[C:14]2=[C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:16]=[CH:17][N:13]2[N:12]=[C:11]([C:24]2[CH:25]=[N:26][CH:27]=[C:28]([CH:32]=2)[C:29](O)=[O:30])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:57]1[CH2:61][CH2:60][CH2:59][C... | COC(=O)C1CCCN1 | O=C(O)c1cncc(-c2nc(NCc3ccccc3)c3c(-c4ccccc4)ccn3n2)c1 | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | CN(C)c1ccncc1 | F[P-](F)(F)(F)(F)F | 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 | 0.17 | To a stirred solution of 5-(4-(benzylamino)-5-phenylpyrrolo[2,1-f][1,2,4]triazin-2-yl)nicotinic acid (80.0 mg, 0.190 mmol) (prepared as in Example 12) in DMF (2 mL), were added DMAP (35.0 mg, 0.285 mmol) and HATU (108 mg, 0.285 mmol) and the reaction mixture was stirred for 10 minutes. Methyl pyrrolidine-2-carboxylate ... | COC(=O)C1CCCN1C(=O)c1cncc(-c2nc(NCc3ccccc3)c3c(-c4ccccc4)ccn3n2)c1 | null | 59.3 | null |
1,758,089 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [CH3:1][C:2]([CH3:77])=[CH:3][CH2:4][CH2:5][C@:6]([O:54][C@@H:55]1[O:60][C@H:59]([CH2:61][O:62][C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H:58]([OH:74])[C@H:57]([OH:75])[C@H:56]1[OH:76])([C@@H:8]1[C@H:12]2[C@H:13]([OH:52])[CH2:14][C@@H:15]3[C@@:20]4([CH3:50])[CH2:21][CH2:22][C@H:23]([O:27][C@@H:28]5[O:33][C@H:32]([C... | CC(C)=CCC[C@](C)(O[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O)[C@H]1CC[C@]2(C)[C@@H]1[C@H](O)C[C@@H]1[C@@]3(C)CC[C@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C(C)(C)[C@@H]3CC[C@]12C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | null | null | 200 g ginsenoside Rb1 with high purity is taken into reaction vessel, 500 ml of purified water is added, and alpha-galactosidase is added, it is decomposed by enzymolysis at 30° C. for 4˜44 hours (more preferably 8˜12 hours, extracted with 200 ml n-butanol for three times, and the n-butanol is combined, concentrated un... | CC(C)=CCC[C@](C)(O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H]1CC[C@]2(C)[C@@H]1[C@H](O)C[C@@H]1[C@@]3(C)CC[C@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C(C)(C)[C@@H]3CC[C@]12C | null | 96.1 | null |
1,187 | ord_dataset-a0eff6fe4b4143f284f0fc5ac503acad | null | 1976-01-01T00:01:00 | true | [CH3:1][C:2]([CH3:7])([CH3:6])[C:3](=[O:5])[CH3:4].C(O)C.[F:11][C:12]([F:16])([F:15])[S:13]Cl>ClCCl>[F:11][C:12]([F:16])([F:15])[S:13][CH2:4][C:3](=[O:5])[C:2]([CH3:7])([CH3:6])[CH3:1] | CC(=O)C(C)(C)C | FC(F)(F)SCl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCO | null | null | null | null | null | null | null | null | null | 25 | null | A mixture of 3,3-dimethyl-2-butanone (1.13 mole), ethanol (1.5 g.) and dichloromethane (300 ml) was introduced into a sealed and pressure tested 2-liter vessel under reduced pressure. Trifluoromethanesulfenyl chloride (1.05 mole) was then added to the cooled, evacuated vessel. (Caution: It should be noted that trifluor... | CC(C)(C)C(=O)CSC(F)(F)F | null | null | null |
319,980 | ord_dataset-0c61835e3a0b4986aabf2b61b708e322 | null | 1995-01-01T00:11:00 | true | [CH:1]([C:15]1[NH:19][CH:18]=[C:17]([C:20]([OH:22])=[O:21])[CH:16]=1)=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]>[Pd].C(O)C>[CH2:1]([C:15]1[NH:19][CH:18]=[C:17]([C:20]([OH:22])=[O:21])[CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][... | CCCCCCCCCCCCC=Cc1cc(C(=O)O)c[nH]1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | An ethanol solution (20 ml) of 3.05 g (10 mmol) of 5-(1-tetradecenyl)pyrrole-3-carboxylic acid prepared in the same manner as in Synthetic Example 7 was subjected to catalytic reduction for 2 hours in the presence of 300 mg of 10% palladium black. After removing the solvent the preduct was crystallized from heptane to ... | CCCCCCCCCCCCCCc1cc(C(=O)O)c[nH]1 | null | 81.3 | null |
1,585,366 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=2[F:21])([OH:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:25]>O1CCCC1>[Cl:20][C:16]1[C:15]([F:21])=[C:14]([C:10]2([O:13][CH3:25])[CH2:11][CH2:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2... | CC(C)(C)OC(=O)N1CCC(O)(c2cccc(Cl)c2F)C1 | CI | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | Preparation according to Preparation 2. Tert-butyl-3-(3-chloro-2-fluorophenyl)-3-hydroxypyrrolidin-1-carboxylate (8.05 g, 25.5 mmol) in dry tetrahydrofuran (50 mL), sodium hydride (60% dispersion in mineral oil, 1.53 g, 38.2 mmol), iodomethane (3.17 mL, 51 mmol). Purification by flash column chromatography on silica ge... | COC1(c2cccc(Cl)c2F)CCN(C(=O)OC(C)(C)C)C1 | null | 76.7 | null |
1,430,181 | ord_dataset-5e6956e6e8c24a168866a253f4a66c6c | null | 2014-01-01T00:05:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([S:13]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=2[CH3:23])(=[O:15])=[O:14])[CH2:10][C@H:9]1[C:24]([OH:26])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.Cl.[NH2:29][C@@H:30]([CH2:39][CH3:40])[C@H:31]([OH:38])[C:32]([NH:34][CH:35]1[CH2:37][CH2:36]1)=[O:33].C(N(CC)C(C)C)(C)C.CN... | Cc1ccc(S(=O)(=O)[C@@H]2C[C@@H](C(=O)O)N(C(=O)OC(C)(C)C)C2)c(C)c1 | CC[C@H](N)[C@H](O)C(=O)NC1CC1 | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | Cl | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 8 | (2S,4R)-1-(tert-butoxycarbonyl)-4-(2,4-dimethylphenylsulfonyl)pyrrolidine-2-carboxylic acid (120 mg, 313 μmol, Eq: 1.00, prepared as described in U.S. Pat. Appl. US20100267722), (2S,3S)-3-amino-N-cyclopropyl-2-hydroxypentanamide dihydrochloride (99.7 mg, 407 μmol, Eq: 1.3), N,N-diisopropylethylamine (121 mg, 164 μA, 93... | CC[C@H](NC(=O)[C@@H]1C[C@@H](S(=O)(=O)c2ccc(C)cc2C)CN1C(=O)OC(C)(C)C)[C@H](O)C(=O)NC1CC1 | null | null | null |
500,880 | ord_dataset-d673d02cdac14dba9ff59f12845a4f37 | null | 2001-01-01T00:05:00 | true | [C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li:13])CCC>>[Li:13][C:8]#[C:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1 | [Li]CCCC | C#Cc1ccccc1 | 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 | Phenylacetylene is reacted with one equivalent of butyllithium at −78° C. to give lithiophenylacetylene. Two equivalents of lithiophenylacetylene are reacted with 1,7-bis(chlorotetrwrnethyldisiloxyl)-m-carborane to give 1,7-bis(phenylacetylenetetramethyldisiloxyl)-m-carborane. This latter material can be used in the hy... | [Li]C#Cc1ccccc1 | null | null | null |
685,367 | ord_dataset-359b8fc87f4244be89d6f02bc5036eac | null | 2005-01-01T00:09:00 | true | [C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=1[NH2:16])([CH3:4])([CH3:3])[CH3:2].C([O:22][C:23](=O)[CH2:24][C:25](=[O:38])[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]2[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=2)[CH:27]=1)(C)(C)C>>[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[CH:13]=[CH:12][... | COc1ccc(NC(=O)OC(C)(C)C)c(N)c1 | CC(C)(C)OC(=O)CC(=O)c1cccc(-c2ccncc2)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 (2-amino-4-methoxy-phenyl)-carbamic acid tert-butyl ester (Example J9) and 3-oxo-3-(3-pyridin-4-yl-phenyl)-propionic acid tert-butyl ester (Example K2) according to the general procedure M. Obtained as a light yellow solid (258 mg). | COc1ccc(NC(=O)OC(C)(C)C)c(NC(=O)CC(=O)c2cccc(-c3ccncc3)c2)c1 | null | null | null |
537,522 | ord_dataset-1884c7bf3d544afdb8d17b5d41b90a27 | null | 2002-01-01T00:03:00 | true | [NH2:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([C:10](=[O:15])N(C)OC)=[CH:6][N:5]2[C:16]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Br[C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1>>[NH2:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([C:10](=[O:15])[C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)=[CH:6][N:5]2[C:... | Fc1ccc(Br)cc1 | CON(C)C(=O)c1ccc2nc(N)c(-c3ccccc3)n2c1 | 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 2-amino-3-phenyl-6-(N-methyl-N-methoxycarbamoyl)imidazo[1,2-a]pyridine (584 mg, 1.97 mmol) and 1-bromo-4-fluorobenzene were converted to product in a manner substantially analogous to Example 141 to yield 205 mg. (52%). NMR (200 MHz, CDCl3) d 4.31 (bs, 2H, NH), 7.15 (m, 2H, F—ArH ), 7.25-7.56 (m, 7H, ArH+H7+H8), 7.... | Nc1nc2ccc(C(=O)c3ccc(F)cc3)cn2c1-c1ccccc1 | null | null | null |
458,181 | ord_dataset-2501595af7f242268dbaab34c9e7ae56 | null | 2000-01-01T00:02:00 | true | [CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([NH:9][C:10](=[S:18])OC2C=CC=CC=2)=[C:4]([O:19][CH3:20])[CH:3]=1.[Cl:21][C:22]1[CH:23]=[C:24]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[CH:25]=[C:26]([Cl:28])[CH:27]=1>>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([NH:9][C:10]([N:32]2[CH2:31][CH2:30][N:29]([C:24]3[CH:23]=[C:22]... | Clc1cc(Cl)cc(N2CCNCC2)c1 | COc1cc(C)c(C)cc1NC(=S)Oc1ccccc1 | 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 | Phenyl N-(4,5-dimethyl-2-methoxyphenyl)thiocarbamate and 1-(3,5-dichlorophenyl)piperazine were reacted by the same way with the example 197 to obtain the titled compound. | COc1cc(C)c(C)cc1NC(=S)N1CCN(c2cc(Cl)cc(Cl)c2)CC1 | null | 85 | null |
813,756 | ord_dataset-892acf7477db4d3a8a8559f004a7c0a2 | null | 2008-01-01T00:03:00 | true | Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH3:13])([CH3:12])[C:9](=[O:11])[N:10]=2)[CH:7]=1.[CH3:14][O:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1>>[CH3:14][O:15][C:16]1[CH:21]=[C:20]([C:2]2[CH:3]=[CH:4][C:5]3[N:6]([C:8]([CH3:13])([CH3:12])[C:9](=[O:11])[N:10]=3)[CH:7]=2)[CH:19]=[CH:18][CH:17]=1 | COc1cccc(B(O)O)c1 | CC1(C)C(=O)N=C2C=CC(Br)=CN21 | 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 54% yield according to the procedure described in Example 2, starting from 6-bromo-3,3-dimethyl-imidazo[1,2-a]pyridin-2-one and 3-methoxyphenyl boronic acid. 1H NMR (CDCl3) δ7.86 (dd, J=2.1 and 9.2 Hz, 1H), 7.73 (d, J=1.5 Hz, 1H), 7.43-7.39 (m, 1H), 7.28-7.25 (m, 1H), 7.05 (m, 1H), 6.... | COc1cccc(C2=CN3C(=NC(=O)C3(C)C)C=C2)c1 | null | 54 | null |
230,644 | ord_dataset-67c9ee844bf341888b345c8e36183b40 | null | 1991-01-01T00:07:00 | true | [C:1]([OH:20])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[NH2:21][C:22]([CH3:26])([CH3:25])[CH2:23]O>>[CH3:23][C:22]1([CH3:26])[CH2:25][O:20][C:1]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH... | CCCCCCCCCCCCCCCCCC(=O)O | CC(C)(N)CO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following example 8, 14.9 g (52.4 mmoles) of octadecanoic acid and 9.34 g (104.8 mmoles) of 2-amino-2-methylpropanol gave 14.1 g (79.7%) of product, b.p. 140°-143° C./0.01 mm Hg. | CCCCCCCCCCCCCCCCCC1=NC(C)(C)CO1 | null | 79.7 | null |
1,122,639 | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | null | 2012-01-01T00:01:00 | true | [Br:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[CH:23]=[C:22]([CH3:24])[O:21][N:20]=3)[CH2:14][CH2:13]2)=[C:4]([N+:9]([O-])=O)[C:5]([NH2:8])=[N:6][CH:7]=1.CCO.[N:28]1([CH2:34][C:35]2[CH:42]=[CH:41][C:38]([CH:39]=O)=[CH:37][CH:36]=2)[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>C... | O=Cc1ccc(CN2CCOCC2)cc1 | Cc1cc(CN2CCN(c3c(Br)cnc(N)c3[N+](=O)[O-])CC2)no1 | null | O=S([O-])S(=O)[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | CCOCC | null | null | null | null | null | null | null | null | null | 80 | 19 | To a mixture of 5-bromo-4-[4-(5-methyl-isoxazol-3-ylmethyl)-piperazin-1-yl]-3-nitro-pyridin-2-ylamine (0.044 g, 0.11 mmol) and EtOH (3.5 ml) was added 4-morpholin-4-ylmethyl-benzaldehyde (0.029 g, 0.14 mmol) followed by a freshly prepared aqueous solution of Na2S2O4 (1M; 0.44 ml, 0.44 mmol). The reaction mixture was st... | Cc1cc(CN2CCN(c3c(Br)cnc4[nH]c(-c5ccc(CN6CCOCC6)cc5)nc34)CC2)no1 | null | null | null |
527,213 | ord_dataset-293186f5c9b441cab57f03cd3a18ac26 | null | 2001-01-01T00:11:00 | true | Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[CH3:9].C([O-])([O-])=O.[K+].[K+].C1(C)C=CC=CC=1.[CH2:23]([O:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=... | Cc1ccc(C)c(Br)c1 | CCCCCCOc1ccc(B(O)O)cc1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | 85 | 20 | Bromo-p-xylene (8.3 g, 45 mmol) (cf. A1 a)), K2CO3 (12.4 g, 90 mmol), 70 ml of toluene and 70 ml of H2O were placed in a reaction vessel and argon was passed in for 30 minutes. 4-hexyloxyphenylboronic acid (10 g, 45 mmol) and Pd(PPh3)4 (0.65 g, 0.56 mmol) were subsequently added under protective gas. The yellow-green, ... | CCCCCCOc1ccc(-c2cc(C)ccc2C)cc1 | null | null | null |
956,366 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | [H-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]([N+:22]([O-:24])=[O:23])=[C:8]2[C:12]=1[NH:11][C:10]([CH3:13])=[C:9]2[O:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1.[C:25]([O:29][C:30](=[O:33])[CH2:31]Br)([CH3:28])([CH3:27])[CH3:26]>C1COCC1>[CH3:26][C:25]([O:29][C:30](=[O:33])[CH2:31][N:11]1[C:12]2[C:8](=[C:7]([... | CC(C)(C)OC(=O)CBr | Cc1[nH]c2c(Br)ccc([N+](=O)[O-])c2c1Oc1ccc(Cl)cc1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 1 | Sodium hydride (60% disp. in oil) (0.043 g) was added to a stirred solution of the product from step (ii) (0.34 g) in THF (4 ml) at RT. After 1 h, tert-butylbromoacetate (170 ul) was added, the mixture stirred at RT for 16 h then quenched with water and extracted with diethylether. The organics were dried and evaporate... | Cc1c(Oc2ccc(Cl)cc2)c2c([N+](=O)[O-])ccc(Br)c2n1CC(=O)OC(C)(C)C | null | null | null |
1,488,482 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[C:10]12([NH2:15])[CH2:14][CH:12]([CH2:13]1)[CH2:11]2>C(#N)C>[C:10]12([NH:15][C:3]3[C:2]([Br:1])=[CH:7][N:6]=[C:5]([Cl:8])[N:4]=3)[CH2:14][CH:12]([CH2:13]1)[CH2:11]2 | NC12CC(C1)C2 | Clc1ncc(Br)c(Cl)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | 25 | 18 | To a solution of 5-Bromo-2,4-dichloro-pyrimidine (6 g, 26.3 mmol) and bicyclo[1.1.1]pent-1-ylamine (4.7 g, 39.5 mmol) in acetonitrile (60 mL), was added TEA (16.5 mL, 118 mmol), and the mixture was stirred at 25° C. for 18 hours. The volatiles were removed in vacuo and the residue partitioned between water and EtOAc. T... | Clc1ncc(Br)c(NC23CC(C2)C3)n1 | null | 82 | null |
797,147 | ord_dataset-a2d74266062e4398bc26c4f876903ab8 | null | 2007-01-01T00:11:00 | true | [CH3:1][C:2]1[C:3]([CH2:9][NH:10][C@@H:11]2[C:20]3[N:19]=[CH:18][CH:17]=[CH:16][C:15]=3[CH2:14][CH2:13][CH2:12]2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[CH3:21][O:22][C:23](=[O:34])[C:24]1[CH:29]=[C:28]([C:30]#[N:31])[CH:27]=[CH:26][C:25]=1[CH2:32]Br.CCN(C(C)C)C(C)C>CC#N>[CH3:21][O:22][C:23](=[O:34])[C:24]1[CH:29]=[C:28](... | Cc1cnc(CN[C@H]2CCCc3cccnc32)c(C)c1 | COC(=O)c1cc(C#N)ccc1CBr | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | null | Using General Procedure A: Reaction of (S)-(3,5-dimethyl-pyridin-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine in CH3CN with 2-Bromomethyl-5-cyano-benzoic acid methyl ester, DIPEA and KI gave 5-cyano-2-{[(3,5-dimethyl-pyridin-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8yl)amino]-methyl}-benzoic acid methyl ester a... | COC(=O)c1cc(C#N)ccc1CN(Cc1ncc(C)cc1C)C1CCCc2cccnc21 | null | null | null |
790,273 | ord_dataset-530502f8e61e455784f93c5faa45c94b | null | 2007-01-01T00:09:00 | true | [CH3:1][O:2][C:3]1[C:8]([CH:9]([C:11]2[CH:16]=[CH:15][C:14](OC)=[CH:13][CH:12]=2)[OH:10])=[C:7]([CH3:19])[CH:6]=[C:5]([O:20][CH3:21])[N:4]=1.C[C:23](OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=[O:24].C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[CH3:23][O:24][C:16]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:9]([... | COc1ccc(C(O)c2c(C)cc(OC)nc2OC)cc1 | CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21 | null | O=C([O-])O | O=S([O-])([O-])=S | [Na+] | 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 | 0.75 | To a solution of 3-cyano-2,6-dimethoxy-4-methylpyridine (0.11 g) in tetrahydrofuran (3 mL) was added diisobutylaluminum hydride (1.5 mol/L solution in toluene, 0.53 mL) at 0° C. The temperature was raised to room temperature, and the reaction solution was stirred for 5 days. To the reaction mixture was added 1 mol/L hy... | COc1cc(C)c(C(=O)c2ccccc2OC)c(OC)n1 | null | 81.7 | null |
1,119,401 | ord_dataset-4226e9b4f9f845db967ed997270dcafc | null | 2011-01-01T00:12:00 | true | [CH2:1]([O:8][C:9]1[C:14]([N+:15]([O-])=O)=[CH:13][C:12]([F:18])=[CH:11][C:10]=1[F:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[Cl-].[NH4+]>CCO.[Zn]>[CH2:1]([O:8][C:9]1[C:10]([F:19])=[CH:11][C:12]([F:18])=[CH:13][C:14]=1[NH2:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1 | O=[N+]([O-])c1cc(F)cc(F)c1OCc1ccccc1 | null | null | [Cl-] | [NH4+] | [Zn] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCO | null | null | null | null | null | null | null | null | null | 60 | null | To a solution of 2-benzyloxy-1,5-difluoro-3-nitrobenzene (2.60 g, 9.80 mmol) in EtOH (20 mL)/water (10 mL) is added zinc (3.4 g, 49 mmol) and ammonium chloride (1.0 g, 19.6 mmol) and the mixture is heated at 60° C. for 2 h. The mixture is extracted with EtOAc and the solvent is removed under reduced pressure. The resid... | Nc1cc(F)cc(F)c1OCc1ccccc1 | null | null | null |
1,698,304 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | Br[C:2]1[C:3]([Cl:18])=[C:4]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:5]=[C:6]([C:8]#[N:9])[CH:7]=1.[Si:19]([O:26][CH2:27][CH:28]1[O:33][CH2:32][CH2:31][NH:30][CH2:29]1)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=... | CC(C)(C)OC(=O)Nc1cc(C#N)cc(Br)c1Cl | CC(C)(C)[Si](C)(C)OCC1CNCCO1 | null | [Pd] | O=C(/C=C/c1ccccc1)/C=C/c1ccccc1 | c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 100 | null | A round bottom flask was charged with tert-butyl (3-bromo-2-chloro-5-cyanophenyl)carbamate (2.020 g, 6.09 mmol), (+/−)-2-(((tert-butyldimethylsilyl)oxy)methyl)morpholine (1.692 g, 7.31 mmol), Pd2(dba)3 (0.558 g, 0.609 mmol) and BINAP (0.379 g, 0.609 mmol) in toluene (20.31 ml). The flask was evacuated and purged with n... | CC(C)(C)OC(=O)Nc1cc(C#N)cc(N2CCOC(CO[Si](C)(C)C(C)(C)C)C2)c1Cl | null | 42 | null |
1,367,960 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][C:14]3([CH2:25][C:24](=[O:26])[C:23]4[C:18](=[CH:19][CH:20]=[C:21](/[CH:27]=[CH:28]/[C:29](O)=[O:30])[CH:22]=4)[O:17]3)[CH2:13][CH2:12]2)[CH:6]=[CH:7][CH:8]=1.[NH2:32][O:33][CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][O:35]1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH... | COc1cccc(CCN2CCC3(CC2)CC(=O)c2cc(/C=C/C(=O)O)ccc2O3)c1 | NOC1CCCCO1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | null | (E)-3-{1′-[2-(3-Methoxy-phenyl)-ethyl]-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid (165 mg, 0.360 mmol) was suspended in DCM (5 ml). TEA (0.075 ml, 0.54 mmol) was added and the clear solution was treated with NH2OTHP following the procedure described in Example 1, Step B, giving (E)-3-{1′-[2-(3-methoxy-phe... | COc1cccc(CCN2CCC3(CC2)CC(=O)c2cc(/C=C/C(=O)NOC4CCCCO4)ccc2O3)c1 | null | null | null |
154,639 | ord_dataset-d1c545e3afc447099315419421478aab | null | 1987-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][CH2:11][C:12](O)=[O:13])=[CH:4][CH:3]=1.[H-].[Li+]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][O:10][CH2:11][CH2:12][OH:13])=[CH:6][CH:7]=1 | O=C(O)COCCc1ccc(Cl)cc1 | null | null | [H-] | [Li+] | 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 2-(4-chlorophenyl)ethoxyacetic acid obtained according to the preceding paragraph was reduced with lithium hydride in a manner analogous to that described in Example 1(b) to give 1.6 g (43%) of 2-[2-(4-chlorophenyl)-ethoxy]ethanol in the form of an oil which was homogeneous according to chromatography. | OCCOCCc1ccc(Cl)cc1 | null | 43 | null |
1,272,769 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [CH2:1]([N:3](C(=O)C1C=CC(O)=CC=1)[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:5]=1[C@@H:14]1[CH2:23][CH2:22][C:21]2[CH:20]=[C:19]([O:24]C(=O)C(C)(C)C)[CH:18]=[CH:17][C:16]=2[CH2:15]1)[CH3:2].Cl[CH2:41][C:42]([N:44]([CH2:46][CH2:47][O:48][CH2:49][CH3:50])[CH3:45])=O>>[CH2:8]([O:10][CH2:41][CH2:42][N... | CCN(C(=O)c1ccc(O)cc1)c1cc(OC)c(OC)cc1[C@@H]1CCc2cc(OC(=O)C(C)(C)C)ccc2C1 | CCOCCN(C)C(=O)CCl | 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 | Synthesized from pivalic acid (R)-6-{2-[ethyl(4-hydroxybenzoyl)amino]-4,5-dimethoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester (16 mg) and 2-chloro-N-(2-ethoxyethyl)-N-methylacetamide (9.8 mg) according to an analogous synthetic method to Example 404 and purified by LC-MS, the title compound (2.3 mg) was obtained. | CCOCCN(C)CCOc1ccc(CCCNc2cc(OC)c(OC)cc2[C@@H]2CCc3cc(O)ccc3C2)cc1 | null | 27.2 | null |
1,199,873 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | [O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][CH:14]([CH:18]([OH:28])[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24](I)=[CH:23][CH:22]=1)[C:15]([OH:17])=[O:16].[O:29]1[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[CH:31]=[C:30]1B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.[Pd]>[O:... | OB(O)c1cc2ccccc2o1 | O=C(O)C(CCN1C(=O)c2ccccc2C1=O)C(O)CCc1ccc(I)cc1 | null | [Pd] | O=C([O-])[O-] | [Cs+] | 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 | 150 | null | A solution of 2-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-3-hydroxy-5-(4-iodophenyl) pentanoic acid (25 mg, 50 μmol) in dimethylformamide (1.0 mL) was added in one portion to a mixture of -benzofuran-2-ylboronic acid (11 mg, 70 μmol) and fibrecat FC1001 (2.71% Pd; 20 mg, 5.0 μmol) in a Smith microwave reaction ... | O=C(O)C(CCN1C(=O)c2ccccc2C1=O)C(O)CCc1ccc(-c2cc3ccccc3o2)cc1 | null | 12.4 | null |
1,152,823 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[C:5]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][CH3:27])[CH:20]=3)[N:6]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)[N:7]=2)[CH:3]=1.[CH:28]1([N:34]=[C:35]=[O:36])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.CCN(CC)CC>ClCCCl>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]... | O=C=NC1CCCCC1 | CCOc1cccc(Nc2c3cc(Cl)ccc3nn2-c2ccc(Cl)cc2)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | In analogy to the procedure described in example 1.2, [5-chloro-2-(4-chloro-phenyl)-2H-indazol-3-yl]-(3-ethoxy-phenyl)-amine was reacted with cyclohexylisocyanate ([3173-53-3]) in 1,2-dichloroethane in the presence of Et3N (3 eq.) for 4 days under reflux conditions to give the title compound as colorless foam. MS: m/e=... | CCOc1cccc(N(C(=O)NC2CCCCC2)c2c3cc(Cl)ccc3nn2-c2ccc(Cl)cc2)c1 | null | null | null |
207,239 | ord_dataset-dd1de64954674e17b4b690cac09dc67b | null | 1990-01-01T00:04:00 | true | [NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=[O:7])=[CH:4][CH:3]=1.[CH2:13]([S:16](Cl)(=[O:18])=[O:17])[CH2:14][CH3:15]>N1C=CC=CC=1>[CH2:13]([S:16]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([OH:8])=[O:7])=[CH:11][CH:12]=1)(=[O:18])=[O:17])[CH2:14][CH3:15] | CCOC(=O)c1ccc(N)cc1 | CCCS(=O)(=O)Cl | 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 | null | null | In a manner similar to Preparation 9 react ethyl 4-aminobenzoate with 1-propanesulfonyl chloride and pyridine to obtain the title compound. | CCCS(=O)(=O)Nc1ccc(C(=O)O)cc1 | null | null | null |
750,694 | ord_dataset-844a22e1fcab44a5b59c5e2922b2855a | null | 2007-01-01T00:01:00 | true | [CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][N:5]([C:10]1[CH:11]=[C:12]([N+:16]([O-])=O)[CH:13]=[CH:14][CH:15]=1)[S:6]([CH3:9])(=[O:8])=[O:7]>[Pd]>[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][N:5]([C:10]1[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=1)[NH2:16])[S:6]([CH3:9])(=[O:8])=[O:7] | CN(C)CCN(c1cccc([N+](=O)[O-])c1)S(C)(=O)=O | null | null | [Pd] | 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 | Prepared analogously to Example 1d by catalytic hydrogenation of 1.9 g (6.8 mmol) of 3-[N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino]-nitrobenzene over palladium/charcoal. | CN(C)CCN(c1cccc(N)c1)S(C)(=O)=O | null | null | null |
205,202 | ord_dataset-72fffaae67c8473fb9d951cb1b026646 | null | 1990-01-01T00:03:00 | true | [OH:1][C:2]1[C:14]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:13][C:5]([CH:6]=[N:7][N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)=[CH:4][C:3]=1[C:19]([CH3:22])([CH3:21])[CH3:20].C([BH3-])#N.[Na+]>C(O)(=O)C>[OH:1][C:2]1[C:14]([C:15]([CH3:17])([CH3:16])[CH3:18])=[CH:13][C:5]([CH2:6][NH:7][N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)=[CH:4][C:... | CC(C)(C)c1cc(C=Nn2ccnc2)cc(C(C)(C)C)c1O | null | null | [BH3-]C#N | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 25 | 8 | 0.9 g of 1-(4-hydroxy-3,5-di-tert.-butylbenzylideneamino)imidazole are suspended in 10 ml of glacial acetic acid and treated with 1.61 g of sodium cyanoborohydride, whereby a solution results. The solution is stirred at room temperature overnight and then evaporated in a vacuum. The residue is treated with 10 ml of wat... | CC(C)(C)c1cc(CNn2ccnc2)cc(C(C)(C)C)c1O | null | null | null |
1,370,788 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH3:14])=[N:12][NH:11][C:10](=O)[C:9]=2[C:16]2[C:21]([Cl:22])=[CH:20][C:19]([Cl:23])=[CH:18][N:17]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:26])=O>>[Cl:26][C:10]1[N:11]=[N:12][C:13]([CH3:14])=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:9]=1[C:16]1[C:21]([Cl:22])=[CH:20][... | O=P(Cl)(Cl)Cl | Cc1n[nH]c(=O)c(-c2ncc(Cl)cc2Cl)c1-c1ccc(Cl)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 | 110 | 2 | 0.66 g of 5-(4-chlorophenyl)-4-(3,5-dichloro-2-pyridyl)-6-methyl-2H-pyridazin-3-one and 6 g of phosphorus oxychloride were mixed. The mixture was stirred for 2 hours on an oil bath of 110° C. The reaction mixture was allowed to cool to room temperature, then, concentrated under reduced pressure. To the resultant residu... | Cc1nnc(Cl)c(-c2ncc(Cl)cc2Cl)c1-c1ccc(Cl)cc1 | null | 67.8 | null |
1,740,497 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[N:11]=[C:10]([C:20](O)=[O:21])[CH2:9]2)=[C:4]([F:23])[CH:3]=1.S(Cl)([Cl:26])=O>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[N:11]=[C:10]([C:20]([Cl:26])=[O:21])[CH2:9... | O=S(Cl)Cl | O=C(O)C1=NN(c2ccccc2Cl)C(c2ccc(Br)cc2F)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 | 100 | 2 | 5-(4-Bromo-2-fluoro-phenyl)-1-(2-chloro-phenyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid (2.5 g, 6.3 mmol) prepared in Step 4 was added to thionyl chloride (30.0 mL). The reaction mixture was stirred at 100° C. for 2 hours and then concentrated under reduced pressure. The resulting residue was concentrated under reduc... | O=C(Cl)C1=NN(c2ccccc2Cl)C(c2ccc(Br)cc2F)C1 | null | null | null |
1,469,783 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | [N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[O:12])[CH3:11])([O-:3])=[O:2].[CH:13]([CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1)=O>O1CCCC1.[O-]CC.[Na+].C(O)C>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[O:12])/[CH:11]=[CH:13]\[CH:15]1[CH2:2... | CC(=O)c1ccccc1[N+](=O)[O-] | CC(C)(C)OC(=O)N1CCC(C=O)CC1 | null | CC[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCO | null | null | null | null | null | null | null | null | null | 25 | 18 | 1-(2-Nitrophenyl)ethanone (1.04 g) and tert-butyl 4-formylpiperidine-1-carboxylate (1.47 g) were suspended in dry tetrahydrofuran (20 mL) and 20 drops of sodium ethoxide in ethanol (21% by weight) was added. The reaction mixture was stirred at room temperature for 18 hours and concentrated under reduced pressure to aff... | CC(C)(C)OC(=O)N1CCC(/C=C\C(=O)c2ccccc2[N+](=O)[O-])CC1 | null | 57.3 | null |
534,978 | ord_dataset-b1a34bc8c1204d51a772ed27396c794e | null | 2002-01-01T00:02:00 | true | CC1C=C(C)N=C(C)C=1.Br[CH2:11][C:12]1[CH:17]=[C:16]([O:18][CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[CH:15]=[CH:14][C:13]=1[F:24].CS(C)=[O:27]>>[CH:19]1([O:18][C:16]2[CH:15]=[CH:14][C:13]([F:24])=[C:12]([CH:17]=2)[CH:11]=[O:27])[CH2:23][CH2:22][CH2:21][CH2:20]1 | Fc1ccc(OC2CCCC2)cc1CBr | CS(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1cc(C)nc(C)c1 | null | null | null | null | null | null | null | null | null | null | 150 | null | 1.9 ml of s-collidine (14.3 mmol) are introduced into a solution of 3 g of 2-bromomethyl-4-cyclopentyloxy-1-fluorobenzene (11 mmol) in 65 ml of dimethylsulfoxide. The mixture is heated at 150° C. for 25 minutes and is then cooled to room temperature. The solvent is evaporated off and the title product is isolated by ch... | O=Cc1cc(OC2CCCC2)ccc1F | null | null | null |
170,011 | ord_dataset-37d3220f708c49ad839bab296b722248 | null | 1988-01-01T00:03:00 | true | [NH2:1][CH2:2][C:3]([OH:32])([CH3:31])[CH2:4][O:5][CH2:6][C:7]1[NH:8][C:9]([CH3:30])=[C:10]([C:26]([O:28][CH3:29])=[O:27])[CH:11]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:19]=2[Cl:25])[C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].CN(C)/[CH:35]=[N:36]/[N:37]=[CH:38]/N(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1... | CN(C)/C=N/N=C/N(C)C | CCOC(=O)C1=C(COCC(C)(O)CN)NC(C)=C(C(=O)OC)C1c1cccc(Cl)c1Cl | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 1-amino-3-{[4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyrid-2-yl]methoxy}-2-hydroxy-2-methylpropane (0.25 g), N,N-dimethylformamide azine (0.21 g) and para-toluenesulphonic acid (10 mg) in toluene (10 ml) was heated under reflux for 1.5 hours and then partitioned betwee... | CCOC(=O)C1=C(COCC(C)(O)Cn2cnnc2)NC(C)=C(C(=O)OC)C1c1cccc(Cl)c1Cl | null | 65.1 | null |
1,132,608 | ord_dataset-aaeaab5f3720492494c1cbbdd0ed2820 | null | 2012-01-01T00:02:00 | true | [CH3:1][C:2]1[CH:22]=[C:5]2[C:6]([C@H:10]3[CH2:12][C@@H:11]3[CH2:13][NH:14]C(=O)OC(C)(C)C)=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[ClH:23].CO>CO>[ClH:23].[ClH:23].[CH3:1][C:2]1[CH:22]=[C:5]2[C:6]([C@H:10]3[CH2:12][C@@H:11]3[CH2:13][NH2:14])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1 | Cc1cc2c([C@H]3C[C@@H]3CNC(=O)OC(C)(C)C)cccn2n1 | null | null | Cl | 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 | 15 | To a solution of tert-butyl {[(1S,2S)-2-(2-methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropyl]methyl}carbamate (1.84 g, 6.11 mmol) in methanol (6 mL) was added hydrochloric acid-methanol reagent (manufactured by TCI, 18 mL) solution, and the mixture was stirred at room temperature for 15 hr. The solvent was concentrated und... | Cc1cc2c([C@H]3C[C@@H]3CN)cccn2n1 | null | 100 | null |
79,441 | ord_dataset-0c37e633e9814a6e886187796cacf216 | null | 1981-01-01T00:03:00 | true | [C:1]([NH2:4])(=[NH:3])[CH3:2].[Cl:5][C:6]1[CH:7]=[C:8]([CH:15]=[CH:16][C:17]=1[Cl:18])[CH:9]=[CH:10][S:11](Cl)(=[O:13])=[O:12]>>[Cl:5][C:6]1[CH:7]=[C:8]([CH:15]=[CH:16][C:17]=1[Cl:18])[CH:9]=[CH:10][S:11]([NH:3][C:1](=[NH:4])[CH3:2])(=[O:13])=[O:12] | O=S(=O)(Cl)C=Cc1ccc(Cl)c(Cl)c1 | CC(=N)N | 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 | Reaction of acetamidine with 3,4-dichlorostyrylsulfonyl chloride according to the above procedure affords N-[(3,4-DICHLOROSTYRYL)SULFONYL]ACETAMIDINE, m.p. 197.5°-198.5° C. (corr.), crystallized from acetone-isopropanol. | CC(=N)NS(=O)(=O)C=Cc1ccc(Cl)c(Cl)c1 | null | null | null |
635,724 | ord_dataset-de283386b8034acd99fba96d3c7d3227 | null | 2004-01-01T00:04:00 | true | [NH2:1][C@H:2]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:12]=[C:13]([NH:17][C:18](=[O:22])[CH:19]([CH3:21])[CH3:20])[CH:14]=[CH:15][CH:16]=2)[CH2:7][CH2:6]1.[Cl:29][C:30]1[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=1)[C:33](Cl)=[O:34]>>[Cl:29][C:30]1[CH:31]=[C:32]([CH... | O=C(Cl)c1cccc(Cl)c1 | CC(C)C(=O)Nc1cccc(C2CCN(CC[C@H](N)c3ccccc3)CC2)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 | Prepared by Procedure Q1 and Scheme AC using N-(3-{1-[(3S)-3-amino-3-phenylpropyl]-4-piperidinyl}phenyl)-2-methylpropanamide and 3-chlorobenzoyl chloride: ESMS m/e: 518.3 (M+H)+. | CC(C)C(=O)Nc1cccc(C2CCN(CC[C@H](NC(=O)c3cccc(Cl)c3)c3ccccc3)CC2)c1 | null | null | null |
1,171,387 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | [F:1][C:2]1[C:9]([F:10])=[CH:8][C:7]([F:11])=[CH:6][C:3]=1[CH:4]=O.C(O)(=O)[CH2:13][C:14]([OH:16])=[O:15]>>[F:1][C:2]1[C:9]([F:10])=[CH:8][C:7]([F:11])=[CH:6][C:3]=1[CH:4]=[CH:13][C:14]([OH:16])=[O:15] | O=C(O)CC(=O)O | O=Cc1cc(F)cc(F)c1F | 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 | According to the previously described general procedure (GP1), Knoevenagel condensation (75° C.; 3h20) between 2,3,5-trifluorobenzaldehyde (9.730 g; 60.777 mmol) and malonic acid (12.016 g; 115.477 mmol) gave the product 3-(2,3,5-trifluoro-phenyl)-acrylic acid as a colorless solid (8.310 g; 68%). LC-MS: tR=0.84 min.; [... | O=C(O)C=Cc1cc(F)cc(F)c1F | null | null | null |
816,119 | ord_dataset-50f99930fc41474db226bc80774b38df | null | 2008-01-01T00:04:00 | true | [CH2:1]([N:8]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:9](=[O:19])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:27][C:28]1[CH:37]=[CH:36][CH:35]=[CH:34][C:29]=1[C:30]([O:32][CH3:33])=[O:31].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([N:8]... | CCCCCCN(Cc1ccccc1)C(=O)CCc1ccc(O)cc1 | COC(=O)c1ccccc1CBr | 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 | 66 | 8 | N-benzyl-N-hexyl-3-(4-hydroxyphenyl)propanamide (183 mg, 0.54 mmol), methyl 2-(bromomethyl)benzoate (136 mg, 0.59 mmol) and potassium carbonate (112 mg, 0.81 mmol) were mixed in acetonitrile. The mixture was stirred at 66° C. overnight. The solvent was evaporated under reduced pressure and the residue was dissolved in ... | CCCCCCN(Cc1ccccc1)C(=O)CCc1ccc(OCc2ccccc2C(=O)OC)cc1 | null | 34.6 | null |
1,716,031 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:8](Br)[C:9]#[CH:10].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH2:10]([O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:9]#[CH:8] | Oc1ccccc1 | C#CCBr | 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 | O | null | null | null | null | null | null | null | null | null | 85 | null | Referring to FIG. 39, phenol (14.6 g. 0.155 mol), propargyl bromide (19 m 0.171 mol) and potassium carbonate (32.1 g, 0.232 mol) in DMF (100 mL) were heated at 85° C. overnight. The reaction was diluted with water and extracted with ether. The extract was washed with brine, dried (MgSO4) and evaporated. The residue was... | C#CCOc1ccccc1 | null | 84 | null |
1,390,696 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | OO.[CH:3]([OH:5])=O.[C:6]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)C[CH2:9][CH2:8][CH:7]=1>>[C:11]1([CH:6]2[CH2:7][CH2:8][CH2:9][C:3]2=[O:5])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1 | C1=C(c2ccccc2)CCC1 | O=CO | null | OO | 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 | 40 | 4 | A mixture of 30% hydrogen peroxide (23 mL, 149 mmol) and 85% formic acid (100 mL, 2619 mmol) was heated at 40° C. for 15 minutes. The mixture was carefully added to cyclopentenylbenzene (21.49 g, 149 mmol) and the resulting two-phase system was vigorously stirred at room temperature for 4 h. An exothermic reaction was ... | O=C1CCCC1c1ccccc1 | null | 83.9 | null |
538,117 | ord_dataset-1884c7bf3d544afdb8d17b5d41b90a27 | null | 2002-01-01T00:03:00 | true | [C:1]([NH2:9])(=[S:8])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.Cl[CH:11]([C:17]([CH3:19])=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13]>C(O)C>[CH3:19][C:17]1[N:9]=[C:1]([C:2]2[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=2)[S:8][C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13] | CCOC(=O)C(Cl)C(C)=O | NC(=S)c1ccncc1 | 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 | A mixture of thioisonicotinamide (2.76 g) and ethyl 2-chloroacetoacetate (3.6 g) in ethanol (30 ml) was heated for 20 hours under reflux and the solvent was evaporated. To the residue was added saturated sodium hydrogen carbonate solution, and the solution was extracted with ethyl acetate. The extract was washed with w... | CCOC(=O)c1sc(-c2ccncc2)nc1C | null | 40.3 | null |
1,694,429 | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | null | 2016-01-01T00:02:00 | true | [NH2:1][CH2:2][C:3]12[CH2:9][CH:6]([CH2:7][O:8]1)[N:5](C(OC(C)(C)C)=O)[CH2:4]2.[CH3:17][C:18](OCl)=[O:19]>C(Cl)Cl>[CH:6]12[CH2:9][C:3]([CH2:2][NH:1][C:18](=[O:19])[CH3:17])([O:8][CH2:7]1)[CH2:4][NH:5]2 | CC(C)(C)OC(=O)N1CC2(CN)CC1CO2 | CC(=O)OCl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 2 | A mixture of tert-butyl 4-(aminomethyl)-5-oxa-2-azabicyclo[2.2.1]heptane-2-carboxylate (Wuxi AppTec, CAS 1357351-98-4) (50 mg, 0.22 mmol), TEA (44.4 mg, 0.44 mmol) in DCM (2 mL) was added CH3CO2Cl (26 mg, 0.33 mmol) at 0° C. After 2 hours, the solvent was removed under reduced pressure. The residue was treated with TFA... | CC(=O)NCC12CNC(CO1)C2 | null | null | null |
625,298 | ord_dataset-e44331dc51de453ca14b7032593c1958 | null | 2004-01-01T00:02:00 | true | N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:32][CH2:33][CH2:34][C:35]1[CH:43]=[CH:42][CH:41]=[C:40]2[C:36]=1[CH2:37][C:38](=[O:44])[NH:39]2.[CH:45]([C:48]1[CH:49]=[C:50](O)[CH:51]=[CH:52][CH:53]=1)([CH3:47])[CH3:46]>O1CCCC1>[CH:45]([C:48]1[CH:53]=[C:52]([CH:51]=[CH:50][CH:49]=1)[O:32][CH2:33][CH2:3... | O=C1Cc2c(CCO)cccc2N1 | CC(C)c1cccc(O)c1 | null | CCOC(=O)N=NC(=O)OCC | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 0.25 | Diethyl azodicarboxylate (0.47 mL, 3 mmol) was added to a solution of triphenylphosphine (0.786 g, 3 mmol) in tetrahydrofuran (10 mL) under nitrogen atmosphere. The mixture was stirred for 15 minutes. To it was then added 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (0.53 g, 3 mmol) (Hayler, J. D.; Howic, S. L. B.; Gile... | CC(C)c1cccc(OCCc2cccc3c2CC(=O)N3)c1 | null | 13.5 | null |
1,695,505 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH:2]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1)=[O:1] | O=C(O)Cc1ccc(CO)cc1 | null | null | [Mn+4] | [O-2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 50 | 18 | To [4-(hydroxymethyl)phenyl]acetic acid (3 g, 18 mmol) in CHCl3 (50 mL) under N2 was added manganese dioxide (7.7 g, 90 mmol) and the reaction mixture was stirred at 50° C. for 18 h. The crude was filtered through a pad of celite, washed with DCM (50 mL) and concentrated under reduced pressure to give the desired produ... | O=Cc1ccc(CC(=O)O)cc1 | null | 59.6 | null |
1,214,100 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | [Cl:1][C:2]1[C:3]([C:10]([F:13])([F:12])[F:11])=[CH:4][C:5]([I:9])=[C:6]([CH:8]=1)[NH2:7].[C:14](=O)(OC(Cl)(Cl)Cl)[O:15]C(Cl)(Cl)Cl>O1CCOCC1>[Cl:1][C:2]1[CH:8]=[C:6]([N:7]=[C:14]=[O:15])[C:5]([I:9])=[CH:4][C:3]=1[C:10]([F:13])([F:11])[F:12] | Nc1cc(Cl)c(C(F)(F)F)cc1I | O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl | null | null | 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 | 100 | null | 5-Chloro-2-iodo-4-(trifluoromethyl)aniline D10 (7.7 mmol, 2.2 g), bis(trichloromethyl) carbonate (0.35 eq., 2.7 mmol, 800 mg) were dissolved in 1,4-dioxane (10 ml) and the mixture was heated to 100° C. for 15 minutes; the mixture was then cooled to room temperature and it was filtered. The filtrate was concentrated to ... | O=C=Nc1cc(Cl)c(C(F)(F)F)cc1I | null | null | null |
1,303,471 | ord_dataset-78c3f723155a4347a902b53bcee1524d | null | 2013-01-01T00:06:00 | true | [CH2:1]([OH:19])[CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][OH:18].[CH3:20][C:21]([Si:24](Cl)([CH3:26])[CH3:25])([CH3:23])[CH3:22].N1C=CN=C1>CN(C=O)C>[C:21]([Si:24]([CH3:26])([CH3:25])[O:18][CH2:17][CH2:16][O:15][CH2:14][CH2:13][O:12][CH2:11][CH2:10][O:... | CC(C)(C)[Si](C)(C)Cl | OCCOCCOCCOCCOCCOCCO | null | c1c[nH]cn1 | null | 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 | null | Compound 28c was prepared according to the procedure described hereinabove for Compound 6a, using hexaethylene glycol (5 grams, 17.7 mmol), TBDMSCl (1.65 grams, 11 mmol), and imidazole (0.748 grams, 11 mmol) in DMF (26 ml), yielding 1 gram of the product (14% yield). | CC(C)(C)[Si](C)(C)OCCOCCOCCOCCOCCOCCO | null | null | null |
147,723 | ord_dataset-2069a3db775a4d9f9310aca092ecbad8 | null | 1986-01-01T00:08:00 | true | [N:1]1[O:5][N:4]=[C:3]2[C:6]([CH:10]3[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:14]([C:21]([F:24])([F:23])[F:22])[NH:13][C:12]([CH:25]=[O:26])=[C:11]3[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:7][CH:8]=[CH:9][C:2]=12.[BH4-].[Na+].Cl>C(O)C>[N:1]1[O:5][N:4]=[C:3]2[C:6]([CH:10]3[C:15]([C:16]([O:18][CH2:19][CH3:20])=... | CCOC(=O)C1=C(C=O)NC(C(F)(F)F)=C(C(=O)OCC)C1c1cccc2nonc12 | null | null | Cl | [BH4-] | [Na+] | 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 | 0.17 | A solution of diethyl 4-(4-benzofurazanyl)-2-formyl-1,4-dihydro-6-(trifluoromethyl)-3,5-pyridinedicarboxylate (1.1 g; 2.5 mmoles) in dry ethanol (90 ml) was cooled to 0° and sodium borohydride (0.14 g; 3.7 mmoles) was added portionwise over 3 minutes. After 10 minutes, 10% aqueous hydrochloric acid was added dropwise t... | CCOC(=O)C1=C(CO)NC(C(F)(F)F)=C(C(=O)OCC)C1c1cccc2nonc12 | null | 45.3 | null |
1,050,625 | ord_dataset-dd320ded4b3f4764af39de99491533f7 | null | 2011-01-01T00:04:00 | true | [Cl:1][C:2]1[C:3]([CH:20]([C:31]2[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=2[F:38])[S:21]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)(=[O:23])=[O:22])=[CH:4][C:5]([NH:8]CC2C=CC(OC)=C(OC)C=2)=[N:6][CH:7]=1.C(=O)(O)[O-].[Na+]>FC(F)(F)C(O)=O>[Cl:1][C:2]1[C:3]([CH:20]([C:31]2[CH:36]=[C:35]([F:37])[CH:34]=[CH:3... | COc1ccc(CNc2cc(C(c3cc(F)ccc3F)S(=O)(=O)c3ccc(F)cc3)c(Cl)cn2)cc1OC | null | null | O=C([O-])O | [Na+] | 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 | 65 | 17 | [5-Chloro-4-[(2,5-difluorophenyl)-(4-fluorophenylsulfonyl)methyl]pyridin-2-yl](3,4-dimethoxybenzyl)amine (157 mg, 0.28 mmol) was dissolved in trifluoroacetic acid (5.0 ml). The resulting solution was stirred at 65° C. for 17 hours. After cooling, the reaction mixture was concentrated under reduced pressure. To the resi... | Nc1cc(C(c2cc(F)ccc2F)S(=O)(=O)c2ccc(F)cc2)c(Cl)cn1 | null | 98.6 | null |
1,357,960 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | [C:1]1([S:7]([C:10]2[CH:18]=[CH:17][C:16]3[N:15](COCC[Si](C)(C)C)[C:14]4[CH2:27][CH:28]5[NH:32][CH:31]([C:13]=4[C:12]=3[C:11]=2[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:30][CH2:29]5)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:1]1([S:7]([C:10]2[CH:18]=[CH... | CC(C)(C)OC(=O)c1c(S(=O)(=O)c2ccccc2)ccc2c1c1c(n2COCC[Si](C)(C)C)CC2CCC1N2 | null | null | CCCC[N+](CCCC)(CCCC)CCCC | [F-] | 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 | To a solution of the product of step B (1.28 g, 2.25 mmol) in THF (30 mL) was added a 1M solution of TBAF in THF (12 mL, 12.0 mmol) and the resulting solution heated to reflux overnight. The reaction was concentrated in vacuo to a reduced volume and diluted with a saturated aqueous solution of ammonium chloride followe... | CC(C)(C)OC(=O)c1c(S(=O)(=O)c2ccccc2)ccc2[nH]c3c(c12)C1CCC(C3)N1 | null | 92.2 | null |
264,748 | ord_dataset-a7bd0db0684c464bb02ff6a36065fee3 | null | 1993-01-01T00:03:00 | true | [CH2:1](OC1C=CC=CC=1)[C:2]1C=CC=[CH:4][CH:3]=1.[CH2:15]([N:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[C:29]1([N:22]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:15][C:16]2[C:17]3[C:18](=[CH:1][CH:2]=[CH:3][CH:... | c1ccc(CN(c2ccccc2)c2ccccc2)cc1 | c1ccc(COc2ccccc2)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 | N-phenylnaphthaldimine (2.20 g, 0.010 mol) and benzylphenyl ether (1.84 g, 0.010 mol) were reacted as above for the preparation of benzyldiphenylamine. Aqueous work-up afforded a precipitate which was isolated by filtration and recrystallized from 95% ethanol to yield 2.3 g (74%) of needles, mp 170°-172° C. Anal. calcd... | c1ccc(N(Cc2cccc3ccccc23)c2ccccc2)cc1 | null | 74 | null |
559,506 | ord_dataset-f483e698250b4da0a84f425c7bfa965a | null | 2002-01-01T00:08:00 | true | C(OC([C:8]1[C:9]([NH:22][CH3:23])=[C:10]([CH:19]=[CH:20][CH:21]=1)[O:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=O)(C)(C)C>ClCCl.FC(F)(F)C(O)=O>[CH3:23][NH:22][C:9]1[CH:8]=[CH:21][CH:20]=[CH:19][C:10]=1[O:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16] | CNc1c(OCCCC(=O)OC)cccc1C(=O)OC(C)(C)C | 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 | 1 | A solution of methyl 4-(3-t-butoxycarbonyl-[-methyl]aminophenoxy)butyrate(0.2 g) in a mixture of dichloromethane(1 mL) and trifluoroacetic acid(1 mL) was kept at ambient temperature for 1 h and evaporated to dryness. The residue was treated with water and ethyl acetate and the mixture was stirred while making basic wit... | CNc1ccccc1OCCCC(=O)OC | null | 101.4 | null |
1,471,017 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | [NH:1]1[C:9]2[CH:8]=[CH:7][N:6]=[C:5]([C:10](=[O:12])[CH3:11])[C:4]=2[CH:3]=[CH:2]1.[H-].[Na+].[CH3:15][C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.O>C1COCC1>[S:22]([N:1]1[C:9]2[CH:8]=[CH:7][N:6]=[C:5]([C:10](=[O:12])[CH3:11])[C:4]=2[CH:3]=[CH:2]1)([C:19]1[CH:20]=[CH:21][C:16]([CH3:15])=[CH... | CC(=O)c1nccc2[nH]ccc12 | Cc1ccc(S(=O)(=O)Cl)cc1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | O | null | null | null | null | null | null | null | null | null | 0 | 0.5 | To a mixture of 1-(1H-pyrrolo[3,2-c]pyridin-4-yl)ethanone (680 mg, 4.25 mmol) in anhydrous THF (40 mL) at 0° C. was added NaH (60% in mineral oil, 204 mg, 5.1 mmol). After the mixture was stirred at 0° C. for 30 min, 4-methylbenzene-1-sulfonyl chloride (850 mg, 4.46 mmol) was added. The reaction mixture was stirred at ... | CC(=O)c1nccc2c1ccn2S(=O)(=O)c1ccc(C)cc1 | null | 98.8 | null |
1,671,467 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]2[CH2:19][CH2:18][CH:17]([O:20][C:21]3[N:22]=[CH:23][N:24]=[C:25]4[C:32]=3[C:31]3[C@@H:30]([CH2:33][C:34]#[N:35])[CH2:29][CH2:28][C:27]=3[S:26]4)[CH2:16][CH2:15]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:36][Li].O.OO>CO>[CH2:1]([N:8]1[CH2:9][CH2:10][N:11]... | N#CC[C@H]1CCc2sc3ncnc(OC4CCC(N5CCN(Cc6ccccc6)CC5)CC4)c3c21 | [Li]O | null | OO | 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 | 0 | 4 | To a solution of 2-[(3R)-12-[[4-(4-benzylpiperazin-1-yl)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-3-yl]acetonitrile (270 mg, 0.55 mmol, 1.00 equiv) in methanol (25 mL) were added LiOH.H2O (70 mg) and H2O2 (30%) (1.2 mL). The resulting solution was stirred for 4 h at 0° C. in ... | NC(=O)C[C@H]1CCc2sc3ncnc(OC4CCC(N5CCN(Cc6ccccc6)CC5)CC4)c3c21 | null | 32.4 | null |
1,546,000 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][CH2:9][C:10]2[CH:29]=[CH:28][C:13]3[N:14]=[C:15]([N:17]4[C@@H:21]5[CH2:22][CH2:23][CH2:24][CH2:25][C@H:20]5[O:19][C:18]4([CH3:27])[CH3:26])[S:16][C:12]=3[CH:11]=2)[C:3]=1[N+:30]([O-])=O.CCOC(C)=O>CO.[Pd]>[CH3:26][C:18]1([CH3:27])[N:17]([C:15]2[S:16][C:12]3[CH:11]=[C:10]([CH2:9][NH... | CC1(C)O[C@@H]2CCCC[C@H]2N1c1nc2ccc(CNc3ncnc(Cl)c3[N+](=O)[O-])cc2s1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CO | null | null | null | null | null | null | null | null | null | null | 15 | To a stirred mixture of 6-chloro-N-((2-((3aR,7aR)-2,2-dimethylhexahydrobenzo[d]oxazol-3(2H)-yl)benzo[d]thiazol-6-yl)methyl)-5-nitropyrimidin-4-amine (153 mg, 0.3 mmol) from Step 5 of this Example in MeOH (5 mL) and EtOAc (5 mL) was added Pd 10% wt. on carbon (20 mg, 0.02 mmol). Hydrogen gas was bubbled through the stir... | CC1(C)O[C@@H]2CCCC[C@H]2N1c1nc2ccc(CNc3ncncc3N)cc2s1 | null | 125.9 | null |
17,302 | ord_dataset-d625331704b34593871e69cd09a5cd83 | null | 1976-01-01T00:12:00 | true | [CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:17][C:16](=O)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1.S(Cl)([Cl:21])=O>CN(C)C=O>[Cl:21][C:16]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])[N:17]=1 | Cc1ccccc1-c1nc2ccccc2c(=O)[nH]1 | O=S(Cl)Cl | null | null | null | 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 | null | A mixture of 7.6 g of 2-(2-methylphenyl)quinazolin-4(3H)-one and 55 ml of thionyl chloride was treated with 2.35 g of dimethylformamide as described in Example I. The isolated solid was recrystallized from cyclohexane to give 5.1 g of 4-chloro-2-(2-methylphenyl)quinazoline, m.p. 103°-104°; ir and nmr spectra were consi... | Cc1ccccc1-c1nc(Cl)c2ccccc2n1 | null | null | null |
302,227 | ord_dataset-bfcf5a01f1a04ec585ba3f28cb93c8c9 | null | 1995-01-01T00:01:00 | true | C1C(=O)N(OC(CCCCCN[C:17]([CH2:19][CH2:20][CH2:21][CH2:22][C@@H:23]2[S:27][CH2:26][C@@H:25]3[NH:28][C:29]([NH:31][C@H:24]23)=[O:30])=[O:18])=O)C(=O)C1.P([O-])([O-])([O-])=[O:33]>>[OH:33][C:17]([CH2:19][CH2:20][CH2:21][CH2:22][C@H:23]1[C@@H:24]2[C@@H:25]([NH:28][C:29]([NH:31]2)=[O:30])[CH2:26][S:27]1)=[O:18] | O=C(CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@@H]21)NCCCCCC(=O)ON1C(=O)CCC1=O | O=P([O-])([O-])[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 | OA (manufactured by Sigma Co., 30 mg) was dissolved in 0.1M phosphate buffer (pH 7.0 , 1 ml), thereto was added an NHS-LC-biotin solution (manufactured by Pierce Chemical Co., 12.6 mg/ml 0.1M phosphate buffer, pH 7.0; 100 μl) and the mixture was reacted at 30° C. for 1 hour. Thereafter, the procedure in Example 5 (a) w... | O=C(O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@@H]21 | null | null | null |
1,485,476 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:24][C:25]2[N:30]=[C:29]([CH2:31][N:32]3[CH2:37][CH2:36][N:35](C(OC(C)(C)C)=O)[CH2:34][CH2:33]3)[CH:28]=[CH:27][CH:26]=2)[N:4]=1)[CH3:2].[ClH:45]>C(OCC)(=O)C>[ClH:45... | CCc1nn(Cc2cccc(CN3CCN(C(=O)OC(C)(C)C)CC3)n2)c2cccc(NC(=O)c3cnc4ccccn34)c12 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | 0.75 | To a solution of tert-butyl 4-((6-((3-ethyl-4-(imidazo[1,2-a]pyridine-3-carboxamido)-1H-indazol-1-yl)methyl)pyridin-2-yl)methyl)piperazine-1-carboxylate in ethyl acetate was added hydrogen chloride (1 mL; 4M in dioxane) and the mixture was stirred for 45 minutes. The solvent was removed under reduced pressure and the m... | CCc1nn(Cc2cccc(CN3CCNCC3)n2)c2cccc(NC(=O)c3cnc4ccccn34)c12 | null | null | null |
1,163,748 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | CN(C)[CH:3]=[CH:4][C:5]([C:7]1[CH:8]=[C:9]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[C:12]([O:17][CH3:18])[CH:11]=2)=O.S(O)(O)(=O)=O.[CH3:33][N:34]([CH3:38])[C:35]([NH2:37])=[NH:36].[O-]CC.[Na+].C(OCC)(=O)C>C(O)C>[CH3:33][N:34]([CH3:38])[C:35]1[N:37]=[C:5]([... | COc1ccc2cc(C(=O)C=CN(C)C)cc(NC(=O)OC(C)(C)C)c2c1 | CN(C)C(=N)N | null | CC[O-] | O=S(=O)(O)O | [Na+] | 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 | 80 | null | To a solution of tert-butyl (3-(3-(dimethylamino)acryloyl)-7-methoxynaphthalen-1-yl)carbamate (31) (250 mg, 0.67 mmol), and N,N-dimethylguanidine sulfate (220 mg, 0.8 mmol) in ethanol (10 ml) was added 21% wt sodium ethoxide in ethanol (218 μl, 0.67 mmol). The mixture was heated to 80° C. for 24 hours followed by addit... | COc1ccc2cc(-c3ccnc(N(C)C)n3)cc(NC(=O)OC(C)(C)C)c2c1 | null | 98.8 | null |
478,727 | ord_dataset-21c1b1c06c7e4e09a38b5b1c71a32e52 | null | 2000-01-01T00:10:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[N:6][CH:7]=1.[OH-].[K+].F[B-](F)(F)F.[N+:16]([C:19]1[CH:24]=[CH:23][C:22]([N+:25]#[N:26])=[CH:21][CH:20]=1)([O-:18])=[O:17].C(O)(=O)C>O>[Cl:1][C:2]1[C:7]([N:26]=[N:25][C:22]2[CH:21]=[CH:20][C:19]([N+:16]([O-:18])=[O:17])=[CH:24][CH:23]=2)=[N:6][CH:5]=[C:4]([OH:8])[CH:3]=1 | Oc1cncc(Cl)c1 | N#[N+]c1ccc([N+](=O)[O-])cc1 | null | F[B-](F)(F)F | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | O | null | null | null | null | null | null | null | null | null | null | 1 | To a solution of 5-chloro-3-pyridinol (20.0 g, 0.154 mol, Aldrich) and KOH (13.0 g, 0.232 mol) in 300 mL of water at 0° C. was added p-nitrobenzenediazonium tetrafluoroborate (36.6 g, 0.154 mol, Aldrich). After 1 hour, 50 mL of glacial acetic acid was added, and the bright red precipitate was filtered and air-dried. Ch... | O=[N+]([O-])c1ccc(N=Nc2ncc(O)cc2Cl)cc1 | null | 67.1 | null |
1,155,242 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | CS[C:3]1[NH:8][C:7](=[O:9])[CH:6]=[CH:5][N:4]=1.[F:10][C:11]([F:20])([F:19])[C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][CH:18]=1)[NH2:15]>COCCOCCOC>[F:10][C:11]([F:19])([F:20])[C:12]1[CH:13]=[C:14]([NH:15][C:3]2[NH:8][C:7](=[O:9])[CH:6]=[CH:5][N:4]=2)[CH:16]=[CH:17][CH:18]=1 | Nc1cccc(C(F)(F)F)c1 | CSc1nccc(=O)[nH]1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCOCCOC | null | null | null | null | null | null | null | null | null | null | 25 | 18 | To 2-(methyl-thio)pyrimidine-4(3H)-one, 1, (5 g, 35.21 mmol) in diglyme (25 mL) is added 3-trifluoromethylaniline (5.26 mL, 42.25 mmol). The resulting mixture is heated to reflux and stirred for 18 hours. A solid forms upon cooling the mixture to room temperature. The solid is washed with hexanes to afford 1.9 g (21% y... | O=c1ccnc(Nc2cccc(C(F)(F)F)c2)[nH]1 | null | 21 | null |
1,684,967 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]2([CH:18]=[CH2:19])[CH2:13][C:12](OC)([O:14]C)[CH2:11]2)=[C:4]([I:20])[CH:3]=1.Cl.C([O-])(O)=O.[Na+]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]2([CH:18]=[CH2:19])[CH2:13][C:12](=[O:14])[CH2:11]2)=[C:4]([I:20])[CH:3]=1 | C=CC1(COc2ccc(Br)cc2I)CC(OC)(OC)C1 | null | null | Cl | O=C([O-])O | [Na+] | 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 | 1 | The mixture of 4-bromo-1-[(3,3-dimethoxy-1-vinylcyclobutyl)methoxy]-2-iodobenzene (3.16 g, 6.98 mmol) and 1M aqueous HCl (14 mL) in THF (31 mL) was stirred for ambient temperature for 1 hour. Then the mixture was stirred for 4 hours at 50° C. The mixture was cooled to room temperature and added saturated aqueous NaHCO3... | C=CC1(COc2ccc(Br)cc2I)CC(=O)C1 | null | 102.4 | null |
1,467,441 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([CH2:14][C@@H:15]3[CH2:19][CH2:18][NH:17][CH2:16]3)=[N:12][NH:11][C:10]2=[O:20])=[C:5]([F:21])[CH:4]=1.C(N(CC)C(C)C)(C)C.[C:31](Cl)(=[O:34])[CH2:32][CH3:33]>ClCCl>[Br:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([CH2:14][C@@H:15]3[CH2:19][CH2:18][N:17]([C:31](=[O:34])[CH2:32][C... | CCC(=O)Cl | O=c1[nH]nc(C[C@@H]2CCNC2)n1-c1ccc(Br)cc1F | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 8 | Into a 4 mL screwcap vial was placed 4-(4-bromo-2-fluorophenyl)-5-[(3S)-3-pyrrolidinylmethyl]-2,4-dihydro-3H-1,2,4-triazol-3-one hydrochloride (0.318 mmol). Added to the vial in succession was dichloromethane (3 mL), N,N-diisopropylethylamine (0.916 mmol), and propanoyl chloride (0.319 mmol). The vial was capped and st... | CCC(=O)N1CC[C@@H](Cc2n[nH]c(=O)n2-c2ccc(Br)cc2F)C1 | null | 79.2 | null |
1,664,984 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [CH:1]([C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[O:6][CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=O.[NH2:18][CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClC(Cl)C.C(O)(=O)C>[C:11]([O:10][C:8](=[O:9])[CH2:7][O:6][C:5]1[CH:4]=[C... | CC(C)(C)OC(=O)COc1cccc(C=O)c1 | CC(C)(C)OC(=O)CN | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | CC(Cl)Cl | null | null | null | null | null | null | null | null | null | 25 | 16 | To a solution of tert-butyl (3-formylphenoxy)acetate (1.50 g) in dichloroethane (20.0 mL) were added tert-butyl glycinate (874 mg) and acetic acid (1.09 mL), and then sodium triacetoxyborohydride (2.69 g) was added thereto under ice-cooling. The reaction suspension was stirred at room temperature for 16 hours. To the r... | CC(C)(C)OC(=O)CNCc1cccc(OCC(=O)OC(C)(C)C)c1 | null | 52.9 | null |
1,763,983 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [F:1][C@H:2]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[N:5]1CC1C=CC(OC)=CC=1)[CH3:3]>C(O)(C(F)(F)F)=O>[F:1][C@H:2]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[NH:5]1)[CH3:3] | COc1ccc(CN2C(=O)OC[C@@H]2[C@H](C)F)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 | A solution of (R)-4-((S)-1-fluoroethyl)-3-(4-methoxybenzyl)oxazolidin-2-one (1.98 g 7.8 mmol) in 40 mL TFA was heated at 65° C. for 16 h. The reaction mixture was concentrated to remove TFA. Flash column chromatography (EtOAc/CH2Cl2, 0 to 100%) gave 0.91 g (R)-4-((S)-1-fluoroethyl)-oxazolidin-2-one as a pale brown soli... | C[C@H](F)[C@H]1COC(=O)N1 | null | 87.6 | null |
1,086,146 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | [CH:1]1([NH:7][C:8]([NH:10][C:11]2[N:12]=[C:13]3[C:19]([C:20]([CH3:22])=[CH2:21])=[CH:18][N:17]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:14]3=[N:15][CH:16]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CO.[Pd]>[CH:1]1([NH:7][C:8]([NH:10][C:11]2[N:12]=[C:13]3[C:19]([CH:20]([CH3:21])[CH3:22])=... | C=C(C)c1cn(COCC[Si](C)(C)C)c2ncc(NC(=O)NC3CCCCC3)nc12 | 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 | null | The mixture of 1-cyclohexyl-3-[7-isopropenyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea (70 mg, 0.163 mmol) and Pd/C (17 mg, 0.016 mmol) in MeOH (1.6 mL) was shaked under 50 psi of H2 atmosphere overnight, filtered through a pad of celite, and washed with MeOH. The filtrate was concentrated... | CC(C)c1cn(COCC[Si](C)(C)C)c2ncc(NC(=O)NC3CCCCC3)nc12 | null | null | null |
1,035,261 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | [NH2:1][C:2]1[N:3]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:4]=[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]#[CH:13])[N:6]=1.[N:21]([CH2:24][CH2:25][NH:26][C:27](=[O:41])[C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[CH:30][CH:29]=1)=[N+:22]=[N-:23]>>[NH2:... | CCCCCCCc1ccc(C(=O)NCCN=[N+]=[N-])cc1 | C#CCCCCCc1cn(C(=O)OC(C)(C)C)c(N)n1 | 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 | tert-butyl 2-amino-4-(hept-6-ynyl)-1H-imidazole-1-carboxylate (0.125 g, 0.449 mmol) was reacted with N-(2-azidoethyl)-4-heptylbenzamide (0.129 g, 0.449 mmol) following the general click procedure to give tert-butyl 2-amino-4-(5-(1-(2-(4-heptylbenzamido)ethyl)-1H-1,2,3-triazol-4-yl)pentyl)-1H-imidazole-1-carboxylate 1H ... | CCCCCCCc1ccc(C(=O)NCCn2cc(CCCCCc3cn(C(=O)OC(C)(C)C)c(N)n3)nn2)cc1 | null | null | null |
1,293,792 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[N:7]=[C:8]([Cl:19])[N:9]=[C:10]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[C:11]=2[N:12]=1.[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>>[Cl:19][C:8]1[N:9]=[C:10]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:11]2[N:12]=[C:3]([CH2:2][N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH... | C1COCCN1 | Clc1nc(N2CCOCC2)c2nc(CBr)ccc2n1 | 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 | 4-(6-(Bromomethyl)-2-chloropyrido[3,2-d]pyrimidin-4-yl)morpholine 7 (0.1 g) was reacted with morpholine via General Procedure B to afford quantitative yield of 4-((2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)morpholine. | Clc1nc(N2CCOCC2)c2nc(CN3CCOCC3)ccc2n1 | null | null | null |
652,797 | ord_dataset-fe016e2f90e741a590ad77fd5933161f | null | 2004-01-01T00:11:00 | true | CC1C=CC(S(O[CH2:12][C@H:13]2[CH2:26][O:25][C:16]3[CH:17]=[CH:18][C:19]4[N:20]=[C:21]([CH3:24])[O:22][C:23]=4[C:15]=3[O:14]2)(=O)=O)=CC=1.[F:27][C:28]1[CH:41]=[CH:40][C:31]([C:32]([CH:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)=[O:33])=[CH:30][CH:29]=1.C(O)C.C(O)(=O)/C=C/C(O)=O>CS(C)=O>[F:27][C:28]1[CH:41]=[CH:40][C:3... | O=C(c1ccc(F)cc1)C1CCNCC1 | Cc1ccc(S(=O)(=O)OC[C@H]2COc3ccc4nc(C)oc4c3O2)cc1 | null | O=C(O)/C=C/C(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | CCO | null | null | null | null | null | null | null | null | null | 80 | null | (8R)-2-Methyl-7,8-dihydro[1,4]dioxino[2,3-g][1,3]benzoxazol-8-ylmethyl 4-methylbenzenesulfonate (0.45 g, 1.2 mmole) and 4-(4-fluorobenzoyl)piperidine (0.73 g, 3.54 mmole) were combined in 10 mL of DMSO under nitrogen. This solution was heated to 80° C. under nitrogen for 4 hours. After completion, the reaction was cool... | Cc1nc2ccc3c(c2o1)OC(CN1CCC(C(=O)c2ccc(F)cc2)CC1)CO3 | null | 60.9 | null |
948,368 | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | null | 2010-01-01T00:04:00 | true | [Si:1]([O:8]S(C(F)(F)F)(=O)=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:16][O:17][C:18]([CH:20]1[C:24]([CH3:25])=[CH:23][C:22](=O)[N:21]1C(OC(C)(C)C)=O)=[O:19].N1C(C)=CC=CC=1C>ClCCl>[CH3:16][O:17][C:18]([C:20]1[NH:21][C:22]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[CH:23][C:24]=1[CH3:25]... | COC(=O)C1C(C)=CC(=O)N1C(=O)OC(C)(C)C | CC(C)(C)[Si](C)(C)OS(=O)(=O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | Cc1cccc(C)n1 | null | null | null | null | null | null | null | null | null | 23 | 15 | tert-Butyldimethylsilyltrifluoromethanesulfonate (9.99 ml, 11.49 g, 43.5 mmol, 3.0 equiv) was added to a stirring solution of 3-methyl-5-oxo-2,5-dihydro-pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (3.7 g, 14.5 mmol, 1.0 equiv) and 2,6-lutidine (5.07 ml, 4.66 g, 43.5 mmol, 3.0 equiv) in dichlorometha... | COC(=O)c1[nH]c(O[Si](C)(C)C(C)(C)C)cc1C | null | 88.6 | null |
844,193 | ord_dataset-e2b35e721c2741999b0005d12691f9fe | null | 2008-01-01T00:10:00 | true | [NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.Cl[CH2:11][C:12]([N:14]1[CH2:19][CH2:18][CH:17]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[CH2:16][CH2:15]1)=[O:13]>C(OCC)C>[F:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][CH:17]2[CH2:18][CH2:19][N:14]([C:12](=[O:13])[CH2:11][NH:1][C:2]3[CH:9]=... | N#Cc1ccc(N)cc1 | O=C(CCl)N1CCC(Cc2ccc(F)cc2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | null | null | The title compound is prepared from 4-amino-benzonitrile and 2-chloro-1-[4-(4-fluoro-benzyl)-piperidin-1-yl]-ethanone (Example 197a) according to the method described in Example 206. Melting Point: 204-206° C. (diethylether) | N#Cc1ccc(NCC(=O)N2CCC(Cc3ccc(F)cc3)CC2)cc1 | null | null | null |
280,555 | ord_dataset-140fb5527ff24f97bcf0094c5d100120 | null | 1993-01-01T00:11:00 | true | [CH3:1][C@H:2]1[CH2:8][C:6](=[O:7])[C@H:5]([CH:9]([CH3:11])[CH3:10])[CH2:4][CH2:3]1.[OH:12][CH2:13][CH:14]([CH2:16]O)[OH:15].S([O-])(O)(=O)=O.[K+].O>C1(C)C=CC=CC=1>[CH3:1][C@H:2]1[CH2:8][C:6]2([O:15][CH:14]([CH2:13][OH:12])[CH2:16][O:7]2)[C@H:5]([CH:9]([CH3:11])[CH3:10])[CH2:4][CH2:3]1 | CC(C)[C@@H]1CC[C@@H](C)CC1=O | OCC(O)CO | null | O=S(=O)([O-])O | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | O | null | null | null | null | null | null | null | null | null | null | 7 | In a 2 l three-necked flask there are introduced 308 g of 1-menthone (2 mol), 276 g of glycerol (3 mol) and 5 g of potassium hydrogen sulphate in toluene. This mixture is refluxed in a water separator. After 7 hours, 42 g of water have separated. The mixture is neutralised and distilled. | CC(C)[C@@H]1CC[C@@H](C)CC12OCC(CO)O2 | null | null | null |
390,511 | ord_dataset-44d518e567bd4c039d77233023f78bb2 | null | 1998-01-01T00:01:00 | true | [NH2:1][CH2:2][CH2:3][CH:4]([C:12]1([CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]1=[O:25])[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].C(N(C(C)C)CC)(C)C.[F:39][C:40]1[CH:41]=[C:42]([CH:46]=[CH:47][C:48]=1[F:49])[C:43](Cl)=[O:44]>C(Cl... | O=C(Cl)c1ccc(F)c(F)c1 | CC(C)CC1(C(CCN)C(=O)OC(C)(C)C)CCN(CCc2ccccc2)C1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 0 | 16 | To a solution of tert-butyl α-(2-aminoethyl)-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetate (549 mg, 1.36 mmol), CH2Cl2 (8.4 mL), and diisopropylethylamine (0.29 ml, 1.6 mmol) at 0° C. is added 3,4-difluorobenzoyl chloride (0.21 mL, 1.6 mmol). The solution is stirred at 0° C. for 1 hour and 16 hours at... | CC(C)CC1(C(CCNC(=O)c2ccc(F)c(F)c2)C(=O)OC(C)(C)C)CCN(CCc2ccccc2)C1=O | null | 64.6 | null |
290,092 | ord_dataset-5fb693db3950403e9ce1a516570153bf | null | 1994-01-01T00:05:00 | true | [CH3:1][C:2]1[CH:7]=[CH:6][C:5]([Sn](C)(C)C)=[CH:4][CH:3]=1.Br[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20]>>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-:21])=[O:20])=[CH:4][CH:3]=1 | Cc1ccc([Sn](C)(C)C)cc1 | O=[N+]([O-])c1ccccc1Br | 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 | Prepared from 4-methylphenyltrimethylstannane (Example 69, Step A) and 2-bromonitrobenzene by the procedure described in Example 69, Step B. 1H NMR (200 MHz,CDCl3): 2.39 (s,3H), 7.23 (m,3H), 7.45 (m,3H), 7.58 (t,7 Hz,1H), 7.80 (d,7 Hz,1H). | Cc1ccc(-c2ccccc2[N+](=O)[O-])cc1 | null | null | null |
176,405 | ord_dataset-07db50a3ce6941919df30a9e2898988f | null | 1988-01-01T00:08:00 | true | C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[O:9]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH2:23]([O:25][CH:26]([O:29][CH2:30][CH3:31])[CH2:27]Br)[CH3:24]>CN(C)C=O>[CH2:23]([O:25][CH:26]([O:29][CH2:30][CH3:31])[CH2:27][O:22][C:19]1[CH:18]=[CH:17][C:16]([O:9][C:10]2... | Oc1ccc(Oc2ccccc2)cc1 | CCOC(CBr)OCC | null | O=C([O-])[O-] | [I-] | [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 | 150 | null | 150 g of potassium carbonate and 4 g of finely powdered potassium iodide are added to a solution of 112 g (0.6 mole) of 4-phenoxyphenol and 157.6 g (0.8 mole) of bromoacetaldehyde diethyl acetal in 480 ml of dimethylformamide, and the batch is heated, under nitrogen, for 14 hours at 150° C. The salts are then removed b... | CCOC(COc1ccc(Oc2ccccc2)cc1)OCC | null | null | null |
631,656 | ord_dataset-0a66204fc43e49c2922e6f9107e6b62f | null | 2004-01-01T00:03:00 | true | [NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[H-].[Na+].CC1C=CC(S(O[CH:37]2[CH2:42][CH2:41][N:40]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:39][CH2:38]2)(=O)=O)=CC=1>CN(C=O)C>[C:46... | Cc1ccc(S(=O)(=O)OC2CCN(C(=O)OC(C)(C)C)CC2)cc1 | Nc1ncnc2[nH]cc(-c3ccc(Oc4ccccc4)cc3)c12 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 1 | To a solution of 4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidine (2.0 g, 6.6 mmol) in dry DMF (100 ml) under nitrogen at 0° C. was added NaH (0.264 g, 60% dispersion, 6.6 mmol) and the reaction mixture warmed to room temperature and stirred for 1 hr. Tert-butyl 4-[(4-methylphenyl)sulfonyl]oxy-1-piperidinecarbox... | CC(C)(C)OC(=O)N1CCC(n2cc(-c3ccc(Oc4ccccc4)cc3)c3c(N)ncnc32)CC1 | null | 31.2 | null |
1,541,797 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | Cl[C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][N:24]=1)[C:5]([NH:7][C:8]1[S:9][CH:10]=[C:11]([C:13]2[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=2[CH3:21])[N:12]=1)=[O:6].[CH3:25][N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.O>CN1CCCC1=O>[C:14]1([CH3:21])[CH:15]=[C:16]([CH3:20])[CH:17]=[C:18]([CH3:19])[C:13]=1[C:11]1... | CN1CCNCC1 | Cc1cc(C)c(-c2csc(NC(=O)c3ccnc(Cl)c3)n2)c(C)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN1CCCC1=O | null | null | null | null | null | null | null | null | null | 150 | 16 | A mixture of 2-chloro-N-(4-mesitylthiazol-2-yl)isonicotinamide (300.0 mg, 0.8 mmol, 1.0 equiv) and 1-methylpiperazine (1.12 mL, 10.1 mmol, 12 equiv) in methylpyrrolidone (9.0 mL) was stirred at 150° C. for 16 h. The mixture was poured into icy H2O (15.0 mL) and the resultant solids were filtered to provide N-(4-mesityl... | Cc1cc(C)c(-c2csc(NC(=O)c3ccnc(N4CCN(C)CC4)c3)n2)c(C)c1 | null | 25 | null |
1,283,819 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:34]=[CH:33][C:11]3[N:12]([C:29]([CH3:32])([CH3:31])[CH3:30])[C:13]([C:16]4[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=4[N:23]4[CH:27]=[N:26][C:25]([CH3:28])=[N:24]4)(O)[NH:14][C:10]=3[CH:9]=2)=[CH:4][N:3]=1>CO>[C:29]([N:12]1[C:11]2[CH:33]=[CH:34][C:8]([C:5]3[CH:4]=[N:3][C:2]([N... | Cc1ncn(-c2ccc(Cl)cc2C2(O)Nc3cc(-c4cnc(N)nc4)ccc3N2C(C)(C)C)n1 | null | 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 | 70 | null | A mixture of 5-(2-amino-pyrimidin-5-yl)-1-tert-butyl-2-[5-chloro-2-(3-methyl-1,2,4-triazol-1-yl)-phenyl]-2,3-dihydro-1H-benzimidazol-2-ol plus regiosiomer (25 mg) in MeOH (25 mL) is heated at 70° C. for 16 hours. The reaction mixture is allowed to cool to room temperature and is concentrated under reduced pressure. The... | Cc1ncn(-c2ccc(Cl)cc2-c2nc3cc(-c4cnc(N)nc4)ccc3n2C(C)(C)C)n1 | null | 37 | null |
1,767,653 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [F:1][C:2]1[CH:3]=[CH:4][C:5]([C:29]2[N:34]=[CH:33][CH:32]=[CH:31][N:30]=2)=[C:6]([CH:28]=1)[C:7]([N:9]1[CH2:14][CH2:13][CH2:12][C@@H:11]([CH3:15])[C@H:10]1[CH2:16][N:17]1C(=O)C2C(=CC=CC=2)C1=O)=[O:8].NN.O>CO>[NH2:17][CH2:16][C@@H:10]1[C@H:11]([CH3:15])[CH2:12][CH2:13][CH2:14][N:9]1[C:7]([C:6]1[CH:28]=[C:2]([F:1])[CH:3... | C[C@@H]1CCCN(C(=O)c2cc(F)ccc2-c2ncccn2)[C@@H]1CN1C(=O)c2ccccc2C1=O | null | null | NN | 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 | 25 | null | A stirred solution of the product of Step 228b (274 mg, 0.590 mmol) and NH2NH2.H2O (114 mg, 2.27 mmol) in MeOH (10 mL) was heated to reflux for 2.5 h. After this time, the reaction mixture was cooled to rt then concentrated under reduced pressure. The resulting residue was triturated with a mixture of CH2Cl2/hexanes (1... | C[C@@H]1CCCN(C(=O)c2cc(F)ccc2-c2ncccn2)[C@@H]1CN | null | 93.9 | null |
1,407,335 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | [F:1][C:2]1[C:3]([OH:28])=[C:4]([NH:19][N:20]=[C:21]([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:10]=[N:11][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:13][CH:14]=1.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>N1C=CC=CC=1>[F:1][C:2]1[C:3]([O:28][S:30]([CH3:29])(=[O:32])=[O:31])=[C:4]([NH:19]... | CS(=O)(=O)Cl | CCOC(=O)C(C)=NNc1ccc(Oc2ccc(S(C)(=O)=O)nc2)c(F)c1O | 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 | 0 | 15 | To an ice-cooled and stirred solution of ethyl 2-[(3-fluoro-2-hydroxy-4-{[6-(methylsulfonyl)pyridin-3-yl]oxy}phenyl)hydrazono]propanoate (4.95 g) in pyridine (50 mL) was added methanesulfonyl chloride (1.1 mL), and the mixture was stirred at 4° C. to room temperature for 15 h. The reaction mixture was concentrated in v... | CCOC(=O)C(C)=NNc1ccc(Oc2ccc(S(C)(=O)=O)nc2)c(F)c1OS(C)(=O)=O | null | 92 | null |
1,714,836 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [CH:1]([C:3]1[C:12]([CH3:13])=[C:11]([CH3:14])[C:10]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[CH:9][C:4]=1[C:5](OC)=[O:6])=O.[NH2:24][C@@H:25]1[C@@H:30]([OH:31])[CH2:29][CH2:28][O:27][CH2:26]1.S([O-])([O-])(=O)=O.[Mg+2]>C1COCC1>[CH3:23][O:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][C:10]2[CH... | COC(=O)c1cc(Cc2ccc(OC)cc2)c(C)c(C)c1C=O | N[C@H]1COCC[C@@H]1O | null | O=S(=O)([O-])[O-] | [Mg+2] | 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 | 5 | To a solution of methyl 2-formyl-5-(4-methoxybenzyl)-3,4-dimethylbenzoate (13.5 g) in THF (270 mL) were added (3S,4S)-3-aminotetrahydro-2H-pyran-4-ol (5.06 g) and anhydrous magnesium sulfate (9.99 g), and the mixture was stirred at room temperature for 5 hr. The insoluble substance was removed by filtration, and the fi... | COc1ccc(Cc2cc3c(c(C)c2C)CN([C@H]2COCC[C@@H]2O)C3=O)cc1 | null | 5.2 | null |
715,912 | ord_dataset-c8a367b56b4f406b878f51867b157d19 | null | 2006-01-01T00:06:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:29])[CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([C:17]3[CH:18]=[C:19]([NH:23][C:24](=[O:28])[CH:25]([CH3:27])[CH3:26])[CH:20]=[CH:21][CH:22]=3)[CH2:13][CH2:12]2)=[CH:4][CH:3]=1.[O:30]([C:37]1[CH:42]=[CH:41][C:40](O)=[CH:39][CH:38]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32... | Oc1ccc(Oc2ccccc2)cc1 | CC(C)C(=O)Nc1cccc(C2CCN(CCC(O)c3ccc(Br)cc3)CC2)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 | Prepared by Procedure A and Scheme AN using N-(3-{1-[3-(4-bromophenyl)-3-hydroxypropyl]-4-piperidinyl}phenyl)-2-methylpropanamide and 4-phenoxyphenol: ESMS m/e: 626.6 (M+H)+. | CC(C)C(=O)Nc1cccc(C2CCN(CCC(Oc3ccc(Oc4ccccc4)cc3)c3ccc(Br)cc3)CC2)c1 | null | null | null |
1,250,158 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | CO[C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[N:14][O:15][C:16]=2[CH3:17])=[N:6][CH:5]=1.COC(=O)C1C=CC(OC[C:36]2[C:37]([CH:42]3CCCC3)=[N:38]OC=2C)=NC=1>>[CH:37]([NH:38][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([CH:18]3[C... | COC(=O)c1ccc(OCc2c(C3CCCC3)noc2C)nc1 | COC(=O)c1ccc(OCc2c(C3CCCCC3)noc2C)nc1 | 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 | As described for example 30d, 6-(3-cyclohexyl-5-methyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester (708 mg, 1.5 mmol), instead of 6-(3-cyclopentyl-5-methyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester, was converted to the title compound (19 mg, 4%) which was obtained as a white solid after purification by c... | Cc1onc(C2CCCCC2)c1COc1ccc(C(=O)NC(C)C)cn1 | null | 4 | null |
1,043,061 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | Br[CH2:2][C:3]1[C:11]2[C:10](=[O:12])[NH:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:7][C:6]=2[S:5][CH:4]=1.[C-:18]#[N:19].[Na+].Cl>CN(C=O)C>[C:18]([CH2:2][C:3]1[C:11]2[C:10](=[O:12])[NH:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:7][C:6]=2[S:5][CH:4]=1)#[N:19] | [C-]#N | CCOC(=O)c1nc2scc(CBr)c2c(=O)[nH]1 | null | Cl | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | 12 | To a mixture of ethyl 5-(bromomethyl)-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxylate (2000 mg, 6.31 mmol) in DMF (10 mL) was added sodium cyanide (649 mg, 13.2 mmol) at room temperature, and the mixture was stirred for 12 hr. The reaction mixture was acidified with 1N hydrochloric acid, and extracted with ethyl... | CCOC(=O)c1nc2scc(CC#N)c2c(=O)[nH]1 | null | 18.1 | null |
10,325 | ord_dataset-53cd7fd33c6f4f1c804e187bec94be57 | null | 1976-01-01T00:07:00 | true | [CH3:1][C:2]1[N:7]=[C:6]([CH2:8][S:9][CH2:10][CH2:11][NH2:12])[CH:5]=[CH:4][CH:3]=1.[Cl:13][C:14]1[CH:15]=[C:16]([S:21]([NH:24][C:25](=[N:28][CH3:29])SC)(=[O:23])=[O:22])[CH:17]=[CH:18][C:19]=1[Cl:20]>C(#N)C>[Cl:13][C:14]1[CH:15]=[C:16]([S:21]([NH:24][C:25]([NH:28][CH3:29])=[N:12][CH2:11][CH2:10][S:9][CH2:8][C:6]2[CH:5... | Cc1cccc(CSCCN)n1 | CN=C(NS(=O)(=O)c1ccc(Cl)c(Cl)c1)SC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 6-methyl-2-((2-aminoethyl)thiomethyl) pyridine (3.7 g) and N-(3,4-dichlorobenzenesulphonyl)-N', S-dimethylisothiourea (6.2 g) in acetonitrile (250 ml) was heated under reflux for 48 hours. Concentration, followed by chromatographic purification on a column of alumina afforded N-(3,4-dichlorobenzenesulphon... | CNC(=NCCSCc1cccc(C)n1)NS(=O)(=O)c1ccc(Cl)c(Cl)c1 | null | null | null |
745,544 | ord_dataset-4b705442211b4a3988e26d5f65098160 | null | 2006-01-01T00:12:00 | true | Cl.Cl.[NH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH:4]1[C:9]([OH:11])=[O:10].[OH-].[Na+].[C:14](OC([O-])=O)([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].Cl>O1CCOCC1.O>[C:17]([O:16][C:14]([N:6]1[CH2:7][CH2:8][NH:3][CH:4]([C:9]([OH:11])=[O:10])[CH2:5]1)=[O:15])([CH3:20])([CH3:19])[CH3:18] | O=C(O)C1CNCCN1 | CC(C)(C)OC(=O)OC(=O)[O-] | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | O | null | null | null | null | null | null | null | null | null | 5 | 8 | A mixture of piperazine-2-carboxylic acid dihydrochloride in dioxan (1000 ml) and water (500 ml), at 10–15° C., was treated with aqueous sodium hydroxide solution (50%) over 15 minutes to adjust the pH to 9.1. This mixture was then treated portionwise (0.1 equivalent portions) with tert-butyl dicarbonate (114.6 g) over... | CC(C)(C)OC(=O)N1CCNC(C(=O)O)C1 | null | null | null |
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