Trifluoroacetic acid → HCID 178509974, compound

HRID 2053827Notes

Reaction equation

HRID 2053827 reaction equation
C(OC([NH:8][CH2:9][CH:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15]([C:17]1[CH:43]=[CH:42][C:20]([C:21]([NH:23][CH:24]([C:32]2[NH:36][C:35]3[CH:37]=[CH:38][C:39]([Cl:41])=[CH:40][C:34]=3[N:33]=2)[CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)=[O:22])=[CH:19][C:18]=1[Cl:44])=[O:16])=O)(C)(C)C.FC(F)(F)C(O)=O.ClCCl.CO.N.ClCl>>[NH2:8][CH2:9][CH:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15]([C:17]1[CH:43]=[CH:42][C:20]([C:21]([NH:23][CH:24]([C:32]2[NH:36][C:35]3[CH:37]=[CH:38][C:39]([Cl:41])=[CH:40][C:34]=3[N:33]=2)[CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)=[O:22])=[CH:19][C:18]=1[Cl:44])=[O:16]

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 24526ChlorineHCID 21584172Ammonia methanol dichloromethaneHCID 178453067HCID 178453067, compound

Product 1

HCID 178509974HCID 178509974, compound

Procedure

Prepared analogously to Example 17 from 4-[2-(N-tert-butoxycarbonylaminomethyl)pyrrolidin-1-ylcarbonyl]-3-chloro-N-[1-(5-chloro-1H-benzimidazol-2-yl)-2-(pyridin-2-yl)ethyl]benzamide and trifluoroacetic acid. Yield: 216 mg (85%, mixture of four stereoisomers); Rf value: 0.27 (silica gel; dichloromethane/methanol/ammonia=9:1:0.1); C27H26Cl2N6O2 (537.45); mass spectrum: (M−H)−=535/537/539 (chlorine isotope).

Workup

  1. additionYield: 216 mg (85%, mixture of four stereoisomers)

Sources & evidence

ORD record
ord-7cdac9e514de4d5ba637353ea9b97cf7
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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