Diethylamine → HCID 25152864, compound

HRID 2391573Notes

Reaction equation

HRID 2391573 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:33](=[O:35])[NH2:34])=[C:19]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[C:29]([F:32])([F:31])[F:30])[CH:20]=3)[C:9]=2[CH:8]=1)(=O)=O.[CH2:36]([NH:38][CH2:39][CH3:40])[CH3:37]>ClCCl>[CH2:36]([N:38]([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:33]([NH2:34])=[O:35])=[C:19]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[C:29]([F:32])([F:31])[F:30])[CH:20]=3)[C:9]=2[CH:8]=1)[CH2:39][CH3:40])[CH3:37]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 86647101HCID 86647101, compound2×

Product 1

HCID 25152864HCID 25152864, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 58 mg of [1-(5-carbamoyl-4-{[2-(trifluoromethyl)benzyl]oxy}-2-thienyl)-1H-imidazo[4,5-c]pyridin-6-yl]methyl methanesulfonate (compound A1) in 4 ml of dichloromethane were added 146 mg of diethylamine, and the reaction mixture was stirred at room temperature for 12 h. The mixture was concentrated to dryness under vacuum and the residue was dissolved in acetonitrile/water and purified by preparative HPLC (water/acetonitrile, elution gradient 9/1 to 1/9 (v/v)). After lyophilization the title compound was obtained.

Workup

  1. concentrationThe mixture was concentrated to dryness under vacuum
  2. dissolutionthe residue was dissolved in acetonitrile/water
  3. custompurified by preparative HPLC (water/acetonitrile, elution gradient 9/1 to 1/9 (v/v))

Sources & evidence

ORD record
ord-018788245075495fa7f86075304e9fd2
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

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