Hydrochloric Acid → 2-(2-(4-Formyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetamido)-N-(2-hydroxyethyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide

HRID 1162778Notes

Reaction equation

HRID 1162778 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[S:10][C:9]2[CH2:11][CH2:12][CH2:13][CH2:14][C:8]=2[C:7]=1[C:15]([NH:17][CH2:18][CH2:19][OH:20])=[O:16])=[O:4].C(=O)([O-])[O-].[K+].[K+].[F:27][C:28]([F:37])([F:36])[C:29]1[C:33]([CH:34]=[O:35])=[CH:32][NH:31][N:30]=1.Cl>CN(C=O)C.O>[CH:34]([C:33]1[C:29]([C:28]([F:37])([F:27])[F:36])=[N:30][N:31]([CH2:2][C:3]([NH:5][C:6]2[S:10][C:9]3[CH2:11][CH2:12][CH2:13][CH2:14][C:8]=3[C:7]=2[C:15]([NH:17][CH2:18][CH2:19][OH:20])=[O:16])=[O:4])[CH:32]=1)=[O:35]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 595205252-(2-Bromoacetamido)-N-(2-hydroxyethyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamideHCID 178519884HCID 178519884, compound

Product 1

HCID 595204812-(2-(4-Formyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetamido)-N-(2-hydroxyethyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamideYield 49%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2-(2-Bromoacetamido)-N-(2-hydroxyethyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (2.91 g, 8.06 mmol) was dissolved in DMF (25 mL) and potassium carbonate (2.23 g, 16.11 mmol), followed by 3-(trifluoromethyl)-1H-pyrazole-4-carbaldehyde (1.39 g, 8.46 mmol), added. The mixture was stirred at 60° C. for 25 min after which time the reaction mixture was diluted with water (˜800 mL), then acidified with 5 N HCl until pH 1. During acidification a free flowing solid was obtained which was collected by filtration. NMR analysis indicated ˜60-70% purity of desired product. The solid was successfully triturated with a mixture of DCM/ether to give a light beige solid which was collected by filtration. The mother liquor was concentrated and a second batch obtained using a similar process. The batches were combined to yield the title product (1.76 g, 3.95 mmol, 49%).

Workup

  1. additionadded
  2. customwas obtained which
  3. filtrationwas collected by filtration
  4. customThe solid was successfully triturated with a mixture of DCM/ether
  5. customto give a light beige solid which
  6. filtrationwas collected by filtration
  7. concentrationThe mother liquor was concentrated
  8. customa second batch obtained

Sources & evidence

ORD record
ord-9b60c75964c44bc483edb3c6786c9fff
Source dataset
uspto-grants-2010_10
Patent number
US07820707B2

Reaction notes

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