Cyclopropanesulfonyl chloride → HCID 178527563, compound

HRID 1258682Notes

Reaction equation

HRID 1258682 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][C:3]=1[NH:10][C:11]1[NH:15][C:14]2[CH:16]=[CH:17][C:18]([N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)=[CH:19][C:13]=2[N:12]=1.[CH:25]1([S:28](Cl)(=[O:30])=[O:29])[CH2:27][CH2:26]1>>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][S:28]([CH:25]2[CH2:27][CH2:26]2)(=[O:30])=[O:29])=[CH:4][C:3]=1[NH:10][C:11]1[NH:15][C:14]2[CH:16]=[CH:17][C:18]([N:20]3[CH2:21][CH2:22][CH2:23][CH2:24]3)=[CH:19][C:13]=2[N:12]=1

Participants

3

Reactant 2

HCID 2760919Cyclopropanesulfonyl chlorideHCID 178509822HCID 178509822, compound

Product 1

HCID 178527563HCID 178527563, compound

Procedure

A TEA solution (0.35 M in DMF, 0.1 mL) was added to a 4-Chloro-3-[5-(pyrrolidin-1-yl)-1H-benzimidazol-2-ylamino]-benzylamine solution (0.12 M in MeCN, 0.1 mL, prepared in analogy to example 4d) followed by a cyclopropylsulfonyl chloride solution (0.12 M in MeCN, 0.1 mL). The mixture was stirred overnight and filtered through basic alumina. The solids were washed with DMF/MeOH 9:1 and the combined filtrates were concentrated to give the title compound.

Workup

  1. filtrationfiltered through basic alumina
  2. washThe solids were washed with DMF/MeOH 9:1
  3. concentrationthe combined filtrates were concentrated

Sources & evidence

ORD record
ord-57f94588f33c4c8d92fbcfceabf13530
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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