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

HRID 1986226Notes

Reaction equation

C([N:4]([CH:7]([CH3:9])[CH3:8])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]([OH:28])=O)[C:19]=3[CH:18]=2)[C:14]([Cl:29])=[CH:13][N:12]=1.C1(N)CC1.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>[CH:7]1([NH:4][C:26]([C:25]2[C:19]3[CH:18]=[C:17]([C:15]4[C:14]([Cl:29])=[CH:13][N:12]=[C:11]([Cl:10])[N:16]=4)[S:21][C:20]=3[CH:22]=[CH:23][CH:24]=2)=[O:28])[CH2:9][CH2:8]1

Participants

Conditions

Temperature: 0 °C

Procedure

Diisopropylethylamine (1.42 mL) is added to a stirred suspension of 2-(2,5-dichloro-pyrimidin-4-yl)-benzo[b]thiophene-4-carboxylic acid (2.55 g, 7.84 mmol) in anhydrous dichloromethane (40 mL) at 0° C. under nitrogen to form a solution, followed by sequentially addition of cyclopropylamine (0.570 mL, 8.23 mmol) and powdered 1H-benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (3.64 g, 8.23 mmol). The resultant mixture is allowed to stir at 0° C. for 2 hours, then at ambient temperature for 3 hours. Diethyl ether (35 mL) is added in small portions to the mixture, the mixture is stirred for another 20 minutes before filtration. After drying, the crude title compound (2.45 g) is obtained as a tan solid. It is used without further purification.

Workup

customto form a solution
waitat ambient temperature for 3 hours
stirringthe mixture is stirred for another 20 minutes before filtration
customAfter drying

Sources & evidence

ORD record: ord-7edf60ca1f7f4f04a0803524bd83c02e
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547691B2

Reaction notes

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