Trifluoroacetic acid → HCID 86701432, compound

HRID 537534Notes

Reaction equation

HRID 537534 reaction equation
F[C:2](F)(F)[C:3](O)=O.[CH:8]1([N:14]([CH2:33][C:34]2C=N[C:37]([N:40]3[CH:44]=[C:43]([C:45]([F:48])([F:47])[F:46])[CH:42]=[N:41]3)=[CH:38][CH:39]=2)[C:15]2[N:32]=[CH:31][CH:30]=[CH:29][C:16]=2[C:17]([NH:19][CH2:20][CH2:21][C:22]([O:24]C(C)(C)C)=[O:23])=[O:18])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1>ClCCl>[CH:8]1([N:14]([CH2:33][C:34]2[CH:39]=[CH:38][C:37]([N:40]3[CH:44]=[C:43]([C:45]([F:48])([F:46])[F:47])[CH:42]=[N:41]3)=[CH:3][CH:2]=2)[C:15]2[N:32]=[CH:31][CH:30]=[CH:29][C:16]=2[C:17]([NH:19][CH:20]=[CH:21][C:22]([OH:24])=[O:23])=[O:18])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68157032HCID 68157032, compound

Product 1

HCID 86701432HCID 86701432, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.30 mL) was added to a solution of tert-butyl 3-(2-(cyclohexyl(6-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyridine-3-yl)methylamino)nicotinamido)propanoate (30 mg, 0.052 mmol) in dichloromethane (0.4 mL). The mixture was stirred at room temperature for 2 hours. The reaction was concentrated and the residue was co-evaporated with dichloromethane, ethyl acetate and toluene several times, to give (+/−)-3-(2-(cyclohexyl(4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)methylamino)nicotinamido)propenoic acid, as a solid. 1H NMR (400 MHz, CDCl3, δ): 9.81 (br. s, 1H), 8.94 (hr. s, 1H), 8.31-8.21 (m, 1H), 8.15 (s, 1H), 7.87 (s, 1H), 7.66 (d, J=8.58 Hz, 2H), 7.61-7.51 (m, 1H), 7.39 (d, J=8.39 Hz, 2H), 6.70-6.58 (m, 1H), 4.29-4.17 (m, 1H), 3.69-3.53 (m, 2H), 2.76-2.65 (m, 2H), 2.00-0.91 (m, 11H). MS (M+1): 516.2.

Workup

  1. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-f24168ef5cd447c1bda14cec13ff2dce
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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