Trifluoroacetic acid → HCID 178437134, compound

HRID 1919182Notes

Reaction equation

HRID 1919182 reaction equation
[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].C(OC([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[C:20]1[NH:21][CH:22]=[C:23]([C:25]2[CH:30]=[CH:29][C:28]([C:31]3[CH:36]=[CH:35][C:34]([C:37]#[C:38][C:39]4[NH:43][C:42]([C@@H:44]5[CH2:48][CH2:47][CH2:46][N:45]5C(OC(C)(C)C)=O)=[N:41][CH:40]=4)=[CH:33][CH:32]=3)=[CH:27][CH:26]=2)[N:24]=1)=O)(C)(C)C>ClCCCl>[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].[NH:45]1[CH2:46][CH2:47][CH2:48][C@H:44]1[C:42]1[NH:43][C:39]([C:38]#[C:37][C:34]2[CH:35]=[CH:36][C:31]([C:28]3[CH:29]=[CH:30][C:25]([C:23]4[N:24]=[C:20]([C@@H:16]5[CH2:17][CH2:18][CH2:19][NH:15]5)[NH:21][CH:22]=4)=[CH:26][CH:27]=3)=[CH:32][CH:33]=2)=[CH:40][N:41]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178451920HCID 178451920, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 178437134HCID 178437134, compoundYield 195%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

TFA (0.25 mL, 3.2 mmol) was added to a stirring solution of (S)-tert-butyl 2-(5-((4′-(2-((S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-1H-imidazol-4-yl)biphenyl-4-yl)ethynyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (17.8 mg) in DCE (1 mL) and stirred at rt for 1 h. The crude reaction was concentrated to yield a TFA salt of 2-((S)-pyrrolidin-2-yl)-5-((4′-(2-((S)-pyrrolidin-2-yl)-1H-imidazol-4-yl)biphenyl-4-yl)ethynyl)-1H-imidazole (24 mg).

Workup

  1. customThe crude reaction
  2. concentrationwas concentrated

Sources & evidence

ORD record
ord-804da14a95c344ebb84b7001781da5b3
Source dataset
uspto-grants-2013_12
Patent number
US08618153B2

Reaction notes

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