Cyclopropanecarbonyl chloride → HCID 16222022, compound

HRID 1678496Notes

Reaction equation

HRID 1678496 reaction equation
[O:1]=[S:2]1(=[O:35])[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[CH:29]=[C:28]([C:30](=[NH:33])[NH:31][OH:32])[CH:27]=[CH:26][C:25]=4[CH3:34])=[CH:20][CH:19]=3)=[O:17])=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.[CH:36]1([C:39](Cl)=O)[CH2:38][CH2:37]1>>[O:35]=[S:2]1(=[O:1])[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]3[CH:19]=[CH:20][C:21]([C:24]4[CH:29]=[C:28]([C:30]5[N:33]=[C:39]([CH:36]6[CH2:38][CH2:37]6)[O:32][N:31]=5)[CH:27]=[CH:26][C:25]=4[CH3:34])=[CH:22][CH:23]=3)=[O:17])=[CH:11][CH:10]=2)[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 178425641HCID 178425641, compound

Product 1

HCID 16222022HCID 16222022, compound

Procedure

5′-(N-Hydroxycarbamimidoyl)-2′-methyl-biphenyl-4-carboxylic acid [4-(1,1-dioxo-1lambda*6*-thiomorpholin-4-ylmethyl)-phenyl]-amide (50 mg) and cyclopropylcarbonyl chloride (0.02 ml) was heated in a microwave at 150 C for 40 min. The solvent was then evaporated and the residue purified on silica gel. Gradient elution with 0-30% 20:8:1 CH2Cl2/EtOH/NH3 in CH2Cl2 gave the title compound as a white solid (24 mg).

Workup

  1. customThe solvent was then evaporated
  2. customthe residue purified on silica gel
  3. washGradient elution with 0-30% 20:8:1 CH2Cl2/EtOH/NH3 in CH2Cl2

Sources & evidence

ORD record
ord-e77952c1c95042a2b56cd43134b9de2e
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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