1-Methylpiperazine → 5-{6-[(4-methylpiperazin-1-yl)methyl]-1H-imidazo[4,5-c]pyridin-1-yl}-3-{(1R)-1-[2-(trifluoromethyl)phenyl]ethoxy}thiophene-2-carboxamide

HRID 2391592Notes

Reaction equation

HRID 2391592 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:34](=[O:36])[NH2:35])=[C:19]([O:21][C@@H:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]([F:33])([F:32])[F:31])[CH3:23])[CH:20]=3)[C:9]=2[CH:8]=1)(=O)=O.[CH3:37][N:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1>ClCCl>[CH3:37][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:34]([NH2:35])=[O:36])=[C:19]([O:21][C@@H:22]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=5[C:30]([F:33])([F:32])[F:31])[CH3:23])[CH:20]=4)[C:9]=3[CH:8]=2)[CH2:40][CH2:39]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 86647102[1-(5-carbamoyl-4-{(1R)-1-[2-(trifluoro-methyl)phenyl]ethoxy}-2-thienyl)-1H-imidazo[4,5-c]pyridin-6-yl]methyl methanesulfonate

Product 1

HCID 687706955-{6-[(4-methylpiperazin-1-yl)methyl]-1H-imidazo[4,5-c]pyridin-1-yl}-3-{(1R)-1-[2-(trifluoromethyl)phenyl]ethoxy}thiophene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 3.6 g of [1-(5-carbamoyl-4-{(1R)-1-[2-(trifluoro-methyl)phenyl]ethoxy}-2-thienyl)-1H-imidazo[4,5-c]pyridin-6-yl]methyl methanesulfonate and 3.7 ml of 1-methylpiperazine in 80 ml dichloromethane is stirred at 40° C. for 2 hours. The reaction mixture is concentrated to dryness and the resulting residue is purified by flash chromatography [silica gel, eluent: dichloromethane/methanol/triethylamine, elution gradient 99.7/0/0.3 (v/v/v) to 89.7/10/0.3 (v/v/v)]. The obtained product is filtered through a short plug of Flash-NH2 silica gel [eluent: dichloro-methane/methanol, 9/1 (v/v)] in a further purification step. After evaporation of the solvents, the resulting oil is treated with 5 ml diethyl ether, resulting in precipitation of the product. After filtration the title compound is obtained as white solid.

Workup

  1. concentrationThe reaction mixture is concentrated to dryness
  2. customthe resulting residue is purified by flash chromatography [silica gel, eluent: dichloromethane/methanol/triethylamine, elution gradient 99.7/0/0.3 (v/v/v) to 89.7/10/0.3 (v/v/v)]
  3. filtrationThe obtained product is filtered through a short plug of Flash-NH2 silica gel [eluent: dichloro-methane/methanol, 9/1 (v/v)] in a further purification step
  4. customAfter evaporation of the solvents
  5. additionthe resulting oil is treated with 5 ml diethyl ether
  6. customresulting in precipitation of the product
  7. filtrationAfter filtration the title compound
  8. customis obtained as white solid

Sources & evidence

ORD record
ord-b196f080c2434a439ce1548e40c4bb41
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

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