2-Mercaptoacetamide → HCID 69061081, compound

HRID 734363Notes

Reaction equation

HRID 734363 reaction equation
[C:1]([O:5][C:6](=[O:27])[N:7]([CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[C:19]([CH:21]([F:23])[F:22])[C:18]([C:24]#[N:25])=[C:17](Cl)[N:16]=2)[CH2:11][CH2:10]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[SH:28][CH2:29][C:30]([NH2:32])=[O:31]>CN(C=O)C>[C:1]([O:5][C:6](=[O:27])[N:7]([CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[N:16]=[C:17]3[S:28][C:29]([C:30](=[O:31])[NH2:32])=[C:24]([NH2:25])[C:18]3=[C:19]([CH:21]([F:23])[F:22])[CH:20]=2)[CH2:11][CH2:10]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 129612-MercaptoacetamideHCID 86617023HCID 86617023, compound

Product 1

HCID 69061081HCID 69061081, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of (6′-chloro-5′-cyano-4′-difluoromethyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-methyl-carbamic acid tert-butyl ester (1.1 g, 2.74 mmol) potassium carbonate (1.9 g, 13.7 mmol) in DMF (15 mL) was treated with 2-mercaptoacetamide (solution of 1 g, 11 mmol in 10 mL of methanol), and the reaction mixture was heated in a sealed tube at 80° C. overnight. The reaction mixture was then cooled to room temperature and filtered. The filtrate was treated with water (50 mL) and the resulting precipitate was collected by filtration to provide 1.03 g (82.4%) of [1-(3-amino-2-carbamoyl-4-difluoromethyl-thieno[2,3-b]pyridin-6-yl)-piperidin-4-yl]-methyl-carbamic acid tert-butyl ester as a tan solid.

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. filtrationfiltered
  3. additionThe filtrate was treated with water (50 mL)
  4. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-4a7639ab029a49b18ff057831ee13eaa
Source dataset
uspto-grants-2009_09
Patent number
US07592353B2

Reaction notes

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