Cyclopropanecarbonyl chloride → Azd-7295

HRID 1678500Notes

Reaction equation

HRID 1678500 reaction equation
[CH2:1]([S:4]([N:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[C:33]([NH2:35])[CH:32]=[CH:31][C:30]=4[O:36][C:37]([F:40])([F:39])[F:38])=[CH:25][CH:24]=3)=[O:22])=[CH:16][CH:15]=2)[CH2:9][CH2:8]1)(=[O:6])=[O:5])[CH2:2][CH3:3].C(N(CC)C(C)C)(C)C.[CH:50]1([C:53](Cl)=[O:54])[CH2:52][CH2:51]1>C1COCC1>[CH2:1]([S:4]([N:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[C:33]([NH:35][C:53]([CH:50]5[CH2:52][CH2:51]5)=[O:54])[CH:32]=[CH:31][C:30]=4[O:36][C:37]([F:39])([F:40])[F:38])=[CH:25][CH:24]=3)=[O:22])=[CH:16][CH:15]=2)[CH2:9][CH2:8]1)(=[O:5])=[O:6])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 598223685'-Amino-2'-trifluoromethoxy-biphenyl-4-carboxylic acid {4-[4-(propane-1-sulfonyl)-piperazin-1-ylmethyl]-phenyl}-amide

Product 1

HCID 57339445Azd-7295Yield 32.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 5′-amino-2′-trifluoromethoxy-biphenyl-4-carboxylic acid {4-[4-(propane-1-sulfonyl)-piperazin-1-ylmethyl]-phenyl}-amide (50 mg) in dry THF (1 ml) was treated with N,N-diisopropylethylamine (60 μl) followed by cyclopropane carbonyl chloride (18 mg). After 16 h the mixture was evaporated and the residue purified by chromatography. Gradient elution with 0%-30% 20DCM:8EtOH:1NH3 in DCM over 35 mins gave the title compound as an off-white solid (18 mg).

Workup

  1. customAfter 16 h the mixture was evaporated
  2. customthe residue purified by chromatography
  3. washGradient elution with 0%-30%

Sources & evidence

ORD record
ord-8500c374c40841a18b778d57153e9a29
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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