Trifluoroacetic acid → (R)-1-(2-Fluoro-4-(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-1-carbonyl)phenyl)-3-(pyrrolidin-3-yl)urea

HRID 1807762Notes

Reaction equation

HRID 1807762 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)=[O:9])[CH:5]=[CH:4][C:3]=1[NH:33][C:34](=[O:48])[NH:35][C@@H:36]1[CH2:40][CH2:39][N:38](C(OC(C)(C)C)=O)[CH2:37]1.FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]1[CH:7]=[C:6]([C:8]([N:10]2[CH2:11][CH2:12][N:13]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([C:23]([OH:32])([C:24]([F:26])([F:27])[F:25])[C:28]([F:29])([F:30])[F:31])=[CH:21][CH:22]=3)[CH2:14][CH2:15]2)=[O:9])[CH:5]=[CH:4][C:3]=1[NH:33][C:34]([NH:35][C@@H:36]1[CH2:40][CH2:39][NH:38][CH2:37]1)=[O:48]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59175842(R)-tert-Butyl 3-(3-(2-fluoro-4-(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-1-carbonyl)phenyl)ureido)pyrrolidine-1-carboxylate

Product 1

HCID 59175832(R)-1-(2-Fluoro-4-(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-1-carbonyl)phenyl)-3-(pyrrolidin-3-yl)ureaYield 85.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of (R)-tert-butyl 3-(3-(2-fluoro-4-(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-1-carbonyl)phenyl)ureido)pyrrolidine-1-carboxylate (0.289 mmol, 200 mg) in dichloromethane (5 mL) was added trifluoroacetic acid (7.23 mmol, 824 mg) and the mixture allowed to stir at room temperature for 5 hours. The reaction mixture was purified by strong cation exchange column chromatography to afford the title compound (146 mg). MS (ESI) m/z 592.3 [M+H]+

Workup

  1. customThe reaction mixture was purified by strong cation exchange column chromatography

Sources & evidence

ORD record
ord-5fffe68784ae4027a2db38617d02179c
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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