4-Chlorobenzyl mercaptan → HCID 9999629, compound

HRID 1178701Notes

Reaction equation

HRID 1178701 reaction equation
CC(C)([O-])C.[K+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][SH:15])=[CH:10][CH:9]=1.CS([C:20]1[C:24]([C:25]([NH2:27])=[O:26])=[C:23]([NH:28][C:29]2[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=2)[S:22][N:21]=1)(=O)=O>C1COCC1.O>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][S:15][C:20]2[C:24]([C:25]([NH2:27])=[O:26])=[C:23]([NH:28][C:29]3[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=3)[S:22][N:21]=2)=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 804094-Chlorobenzyl mercaptanHCID 23665647Potassium tert-butoxideHCID 695159803-(Methanesulfonyl)-5-[(pyridin-4-yl)amino]-1,2-thiazole-4-carboxamide

Product 1

HCID 9999629HCID 9999629, compoundYield 8.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Potassium tertbutoxide (318 mg, 2.84 mmol) is dissolved in anhydrous THF (5 mL) and (4-Chlorophenyl)-methanethiol (0.375 mL, 2.84 mmol) is then added and stirred for 30 min room temperature. This resulting solution is then added to a solution of crude 9 (170 mg) dissolved in anhydrous THF (3 mL). The reaction is stirred for 4 hours at room temperature and then heated to 60° C. for 18 hours. The reaction is diluted with water and extracted with a solution containing 5% methanol and 95% methylene chloride (10 mL×3). The combined organics are dried over sodium sulfate, filtered and then concentrated in vacuo. Chromatography (3% MeOH/methylene chloride) provides 3-(4-Chloro-benzylsulfanyl)-5-(pyridin-4-ylamino)-isothiazole-4-carboxylic acid amide (18 mg, 2.5%-2 steps). 1H NMR (d6 DMSO): δ 8.17 (2H, broad s), 7.45 (2H, d, J=8.4 Hz), 7.37 (2H, d, J=8.4 Hz), 6.99 (2H, broad s), 4.32 (2H, s); LRMS (M+): 376.9, (M−): 375.0.

Workup

  1. stirringThe reaction is stirred for 4 hours at room temperature
  2. temperatureheated to 60° C. for 18 hours
  3. extractionextracted with a solution
  4. additioncontaining 5% methanol and 95% methylene chloride (10 mL×3)
  5. dry with materialThe combined organics are dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2246e6588a9e4441a65363464062e69c
Source dataset
uspto-grants-2007_10
Patent number
US07276602B2

Reaction notes

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