Potassium Carbonate → 2-(2-(3-Tert-butyl-4-formyl-1H-pyrazol-1-yl)acetamido)-N-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide

HRID 1162773Notes

Reaction equation

[C:1]([C:5]1[C:9]([CH:10]=[O:11])=[CH:8][NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:13][C:14]([NH:16][C:17]1[S:21][C:20]2[CH2:22][CH2:23][CH2:24][CH2:25][C:19]=2[C:18]=1[C:26]([NH:28][CH3:29])=[O:27])=[O:15].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:1]([C:5]1[C:9]([CH:10]=[O:11])=[CH:8][N:7]([CH2:13][C:14]([NH:16][C:17]2[S:21][C:20]3[CH2:22][CH2:23][CH2:24][CH2:25][C:19]=3[C:18]=2[C:26]([NH:28][CH3:29])=[O:27])=[O:15])[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 60 °C

Procedure

3-Tert-butyl-1H-pyrazole-4-carbaldehyde (150 mg, 0.986 mmol), 2-(2-bromoacetamido)-N-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (490 mg, 1.478 mmol) and potassium carbonate (545 mg, 3.94 mmol) were mixed with DMF (5 mL) and heated for 3 h at 60° C. The reaction was partitioned between water and EtOAc. Organics were combined and purified by chromatography (0-60%, EtOAc/heptane) to give the title product as a white solid (360 mg, 0.894 mmol, 91%).

Workup

customThe reaction was partitioned between water and EtOAc
custompurified by chromatography (0-60%, EtOAc/heptane)

Sources & evidence

ORD record: ord-03fc124649734b3690d1364af4cb7bfe
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820707B2

Reaction notes

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