Trifluoroacetic acid → N-benzyl-N-[(3-chloropropyl)sulfonyl]-3-cyclohexyl-1-(2-{methyl[2-(methylamino)ethyl]amino}-2-oxoethyl)-2-phenyl-1H-indole-6-carboxamide hydrochloride

HRID 421972Notes

Reaction equation

HRID 421972 reaction equation
[CH2:1]([N:8]([S:48]([CH2:51][CH2:52][CH2:53][Cl:54])(=[O:50])=[O:49])[C:9]([C:11]1[CH:19]=[C:18]2[C:14]([C:15]([CH:42]3[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]3)=[C:16]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[N:17]2[CH2:20][C:21]([N:23]([CH3:35])[CH2:24][CH2:25][N:26](C)[C:27](=O)OC(C)(C)C)=[O:22])=[CH:13][CH:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[ClH:54].[CH2:1]([N:8]([S:48]([CH2:51][CH2:52][CH2:53][Cl:54])(=[O:49])=[O:50])[C:9]([C:11]1[CH:19]=[C:18]2[C:14]([C:15]([CH:42]3[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47]3)=[C:16]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[N:17]2[CH2:20][C:21]([N:23]([CH3:35])[CH2:24][CH2:25][NH:26][CH3:27])=[O:22])=[CH:13][CH:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66674974tert-butyl {2-[{[6-({benzyl[(3-chloropropyl)sulfonyl]amino}carbonyl)-3-cyclohexyl-2-phenyl-1H-indol-1-yl]acetyl}(methyl)amino]ethyl}methylcarbamate

Product 1

HCID 66674879N-benzyl-N-[(3-chloropropyl)sulfonyl]-3-cyclohexyl-1-(2-{methyl[2-(methylamino)ethyl]amino}-2-oxoethyl)-2-phenyl-1H-indole-6-carboxamide hydrochlorideYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the crude tert-butyl {2-[{[6-({benzyl[(3-chloropropyl)sulfonyl]amino}carbonyl)-3-cyclohexyl-2-phenyl-1H-indol-1-yl]acetyl}(methyl)amino]ethyl}methylcarbamate in DCM) (0.09 M) was treated with TFA (140 eq) at 0° C. The reaction was allowed to reach RT in about 1 h. The solvent was then removed in vacuo, a 2 M solution HCl in Et2O was added and the volatiles removed in vacuo. MeCN was added and the precipitate was collected by filtration to afford clean compound (30%). (ES+) m/z 677 (M+H)+

Workup

  1. customThe solvent was then removed in vacuo
  2. additiona 2 M solution HCl in Et2O was added
  3. customthe volatiles removed in vacuo
  4. additionMeCN was added
  5. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-9f3d98762d604c898f427ec9e4ba8453
Source dataset
uspto-grants-2012_01
Patent number
US08101595B2

Reaction notes

Loading…