Cyclopropanecarbonyl chloride → Cyclopropyl-{4-[6-fluoro-2-phenoxymethyl-3-(4-trifluoromethoxy-benzyl)-3H-benzoimidazol-5-yl]-piperazin-1-yl}-methanone

HRID 131234

Reaction equation

HRID 131234 reaction equation
[F:1][C:2]1[C:30]([N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[CH:29][C:5]2[N:6]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=3)[C:7]([CH2:9][O:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:8][C:4]=2[CH:3]=1.[CH:37]1([C:40](Cl)=[O:41])[CH2:39][CH2:38]1>ClCCl>[CH:37]1([C:40]([N:34]2[CH2:35][CH2:36][N:31]([C:30]3[C:2]([F:1])=[CH:3][C:4]4[N:8]=[C:7]([CH2:9][O:10][C:11]5[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=5)[N:6]([CH2:17][C:18]5[CH:19]=[CH:20][C:21]([O:24][C:25]([F:26])([F:27])[F:28])=[CH:22][CH:23]=5)[C:5]=4[CH:29]=3)[CH2:32][CH2:33]2)=[O:41])[CH2:39][CH2:38]1

Participants

4

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 684671025-fluoro-2-phenoxymethyl-6-piperazin-1-yl-1-(4-trifluoromethoxy-benzyl)-1H-benzoimidazole

Product 1

HCID 68466187Cyclopropyl-{4-[6-fluoro-2-phenoxymethyl-3-(4-trifluoromethoxy-benzyl)-3H-benzoimidazol-5-yl]-piperazin-1-yl}-methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

80 mg of 5-fluoro-2-phenoxymethyl-6-piperazin-1-yl-1-(4-trifluoromethoxy-benzyl)-1H-benzoimidazole (0.16 mmol) and 0.033 ml TEA (0.24 mmol) were dissolved in 1.5 ml dichloromethane and treated with 0.019 ml cyclopropanecarbonyl chloride (0.2 mmol). After 2 h stirring at rt, the reaction mixture was diluted with dichloromethane, washed with water, saturated sodium bicarbonate and brine, dried with magnesium sulfate, filtered and concentrated in vacuo, leading to 89 mg yellow solid (98%). MS (ISP) 569.4 (M+H)+.

Workup

  1. washwashed with water, saturated sodium bicarbonate and brine
  2. dry with materialdried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9a0ec64a57c74eff831b7fa012a6c13a
Source dataset
uspto-grants-2008_06
Patent number
US07384945B2

Linked notes

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