Diisopropylethylamine → 2-(2,5-Dichloropyrimidin-4-yl)-benzo[b]thiophene-4-carboxylic acid amide

HRID 1986210Notes

Reaction equation

C([N:4](C(C)C)CC)(C)C.[Cl:10][C:11]1[N:16]=[C:15]([C:17]2[S:21][C:20]3[CH:22]=[CH:23][CH:24]=[C:25]([C:26](O)=[O:27])[C:19]=3[CH:18]=2)[C:14]([Cl:29])=[CH:13][N:12]=1.N.CO.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>ClCCl.C(OCC)C>[Cl:10][C:11]1[N:16]=[C:15]([C:17]2[S:21][C:20]3[CH:22]=[CH:23][CH:24]=[C:25]([C:26]([NH2:4])=[O:27])[C:19]=3[CH:18]=2)[C:14]([Cl:29])=[CH:13][N:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Diisopropylethylamine (0.574 mL) is added to a stirred suspension of 2-(2,5-dichloropyrimidin-4-yl)-benzo[b]thiophene-4-carboxylic acid (1.02 g, 3.14 mmol) in anhydrous dichloromethane (20 mL) at 0° C. under nitrogen to form a clear solution. The solution is treated dropwise with 7M NH3/MeOH (0.493 mL, 3.45 mmol) to form a suspension. Powdered 1H-benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (1.46 g, 3.30 mmol) is added to the mixture and the resultant mixture is allowed to stir at 0° C. for 2 hours and at room temperature for 5 hours. Diethyl ether (15 mL) is added in small portions to the mixture. The mixture is stirred for another 20 minutes before filtration. After drying, the title compound is obtained as a tan solid and is used without further purification (0.994 g).

Workup

customto form a clear solution
customto form a suspension
stirringThe mixture is stirred for another 20 minutes before filtration
customAfter drying

Sources & evidence

ORD record: ord-154c8d82d7fa4c89b79eeec429915c6d
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547691B2

Reaction notes

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