Trifluoroacetic acid → HCID 86731022, compound

HRID 1852487Notes

Reaction equation

HRID 1852487 reaction equation
[C:1]([C:4]1[C:5]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)=[N:6][N:7]([CH:9]2[CH2:14][CH2:13][CH:12]([C:15]([O:17]C(C)(C)C)=[O:16])[CH2:11][CH:10]2[C:22]#[N:23])[CH:8]=1)(=[O:3])[NH2:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]([C:4]1[C:5]([NH:24][C:25]2[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=2)=[N:6][N:7]([CH:9]2[CH2:14][CH2:13][CH:12]([C:15]([OH:17])=[O:16])[CH2:11][CH:10]2[C:22]#[N:23])[CH:8]=1)(=[O:3])[NH2:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86731020HCID 86731020, compound

Product 1

HCID 86731022HCID 86731022, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1S,3S,4S and 1R,3R,4R)-t-butyl 4-[4-carbamoyl-3-[(4-chlorophenyl)amino]-1H-pyrazol-1-yl]-3-cyanocyclohexane-1-carboxylate (500 mg, 1.1 mmol) in DCM (4 mL) was added TFA (2 mL) at 0° C. The resulting solution was stirred at ambient temperature for 16 hours and then concentrated in vacuo to afford the title compound as an off-white solid, which was used directly without further purification. 1H NMR (400 MHz, CD3OD) δ 8.14 (s, 1H), 7.58-7.53 (m, 2H), 7.26-7.21 (m, 2H), 4.32-4.30 (m, 1H), 3.50-3.46 (m, 1H), 2.58-2.48 (m, 2H), 2.33-2.15 (m, 3H), 1.98-1.88 (m, 1H), 1.77-1.64 (m, 1H). MS ESI: [M+H]+ m/z 388.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-93ede96c7a6d44509c2e4d82b74dfe41
Source dataset
uspto-grants-2015_02
Patent number
US08962608B2

Reaction notes

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