Trifluoroacetic acid → Trifluoroacetic acid

HRID 2207381Notes

Reaction equation

HRID 2207381 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[OH:8][C:9]1([C:22]2[CH:23]=[N:24][CH:25]=[C:26]([C:28]3[CH:33]=[C:32]([NH:34][C:35]4[N:40]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:38]=[CH:37][N:36]=4)[CH:31]=[C:30]([CH3:45])[CH:29]=3)[CH:27]=2)[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]1>ClCCl.[NH4+].[OH-]>[CH3:45][C:30]1[CH:29]=[C:28]([C:26]2[CH:27]=[C:22]([C:9]3([OH:8])[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]3)[CH:23]=[N:24][CH:25]=2)[CH:33]=[C:32]([NH:34][C:35]2[N:40]=[C:39]([C:41]([F:43])([F:44])[F:42])[CH:38]=[CH:37][N:36]=2)[CH:31]=1.[C:3]([OH:5])([C:2]([F:7])([F:6])[F:1])=[O:4]

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131735898HCID 131735898, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 72705767HCID 72705767, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14923Ammonium HydroxideSolvent

Procedure

Trifluoroacetic acid (262 μL, 3.40 mmol) was added to a solution of tert-butyl 4-hydroxy-4-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-3-yl]piperidine-1-carboxylate (180 mg, 0.340 mmol) in dichloromethane (1.70 mL). The reaction mixture was stirred for 2 hours, diluted with 10% aqueous NH4OH (1.00 mL) and the precipitated solid was collected by filtration to yield 4-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-3-yl]piperidin-4-ol as a TFA salt. MS APCI calc'd for C22H23F3N5O [M+H]+ 430. found 430. 1H NMR (500 MHz, DMSO-d6) δ 8.82 (d, J=5.2 Hz, 1H), 8.66 (s, 2H), 8.01 (s, 1H), 7.98 (s, 1H), 7.56 (s, 1H), 7.26 (d, J=5.0 Hz, 1H), 7.20 (s, 1H), 3.04-2.92 (m, 2H), 2.76 (br m, 2H), 2.36 (s, 3H), 1.99-1.75 (br m, 2H), 1.69-1.49 (br m, 2H).

Workup

  1. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-f63024a37fef486e8412fb31993d453e
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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