1-(2-(Dimethylamino)ethyl)piperazine → 5-[6-({4-[2-(dimethylamino)ethyl]piperazin-1-yl}methyl)-1H-imidazo[4,5-c]pyridin-1-yl]-3-[(1R)-1-(2-fluorophenyl)ethoxy]thiophene-2-carboxamide

HRID 2391652Notes

Reaction equation

CS(O[CH2:6][C:7]1[N:12]=[CH:11][C:10]2[N:13]=[CH:14][N:15]([C:16]3[S:17][C:18]([C:31](=[O:33])[NH2:32])=[C:19]([O:21][C@@H:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[F:30])[CH3:23])[CH:20]=3)[C:9]=2[CH:8]=1)(=O)=O.[CH3:34][N:35]([CH3:44])[CH2:36][CH2:37][N:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1>ClCCl>[CH3:34][N:35]([CH3:44])[CH2:36][CH2:37][N:38]1[CH2:43][CH2:42][N:41]([CH2:6][C:7]2[N:12]=[CH:11][C:10]3[N:13]=[CH:14][N:15]([C:16]4[S:17][C:18]([C:31]([NH2:32])=[O:33])=[C:19]([O:21][C@@H:22]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=5[F:30])[CH3:23])[CH:20]=4)[C:9]=3[CH:8]=2)[CH2:40][CH2:39]1

Participants

Conditions

Temperature: 40 °C

Procedure

136 mg of crude (1-{5-carbamoyl-4-[(1R)-1-(2-fluorophenyl)ethoxy]-2-thienyl}-1H-imidazo[4,5-c]pyridin-6-yl)methyl methanesulfonate (example 101, step 1) are dissolved in 5 ml dichloromethane. Under N2 atmosphere N,N-dimethyl-2-piperazin-1-ylethanamine (218 mg) is added. The reaction mixture is stirred at 40° C. for 2 hours and 2 hours at room temperature. It is then concentrated to dryness under vacuum. The residue is purified by preparative HPLC (ammonium formate buffer/acetonitrile, elution gradient 97/3 to 0/100 (v/v)) to obtain the title product.

Workup

concentrationIt is then concentrated to dryness under vacuum
customThe residue is purified by preparative HPLC (ammonium formate buffer/acetonitrile, elution gradient 97/3 to 0/100 (v/v))

Sources & evidence

ORD record: ord-0461ffc029ad46fc88b8d56dcbbd4132
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273890B2

Reaction notes

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