Potassium Carbonate → 2-(2-(3-Cyanoindazol-1-yl)acetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide

HRID 1162759

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]#[N:11])=[N:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]([NH:22][C:23]1[S:27][C:26]2[CH2:28][CH2:29][CH2:30][CH2:31][C:25]=2[C:24]=1[C:32]([NH2:34])=[O:33])=[O:21]>CN(C=O)C.O>[C:10]([C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[N:1]([CH2:19][C:20]([NH:22][C:23]2[S:27][C:26]3[CH2:28][CH2:29][CH2:30][CH2:31][C:25]=3[C:24]=2[C:32]([NH2:34])=[O:33])=[O:21])[N:2]=1)#[N:11]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1H-indazole-3-carbonitrile (11 mg, 0.077 mmol) in DMF (500 μL) was added potassium carbonate and the whole was stirred at RT for 30 min before 2-(2-bromoacetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (24 mg, 0.077 mmol) was added. The reaction mixture was heated to 60° C. and this temperature was maintained for 1.5 h before the reaction mixture was cooled to RT, then diluted with water (5 mL). The organics were extracted with diethyl ether (10 mL), EtOAc (10 mL) and DCM (10 mL), then combined and the suspension concentrated to dryness. The residue was dissolved in DMSO (1 mL) and purified by preparative reverse phase HPLC to give the title compound as a white solid (4 mg, 0.01 mmol, 14%).

Workup

additionwas added
temperaturethis temperature was maintained for 1.5 h before the reaction mixture
temperaturewas cooled to RT
extractionThe organics were extracted with diethyl ether (10 mL), EtOAc (10 mL) and DCM (10 mL)
concentrationthe suspension concentrated to dryness
dissolutionThe residue was dissolved in DMSO (1 mL)
custompurified by preparative reverse phase HPLC

Sources & evidence

ORD record: ord-5e422bed1d3342dd8738610cfc62d4ed
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820707B2

Linked notes

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