Trifluoroacetic acid → Trifluoroacetic acid

HRID 2207417Notes

Reaction equation

HRID 2207417 reaction equation
[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].[CH3:8][C:9]1[CH:10]=[C:11]([NH:21][C:22]2[N:27]=[C:26]([O:28][CH:29]3[CH2:34][CH2:33][N:32](C(OC(C)(C)C)=O)[CH2:31][CH2:30]3)[CH:25]=[CH:24][N:23]=2)[CH:12]=[C:13]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:14]=1>ClCCl>[CH3:8][C:9]1[CH:10]=[C:11]([NH:21][C:22]2[N:27]=[C:26]([O:28][CH:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)[CH:25]=[CH:24][N:23]=2)[CH:12]=[C:13]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:14]=1.[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 118092945HCID 118092945, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 118103400HCID 118103400, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA deprotection: 1:1 Dichloromethane:TFA (1.00 mL) solution was added to the isolated tert-butyl 4-[(2-{[3-methyl-5-(pyridin-3-yl)phenyl]amino}pyrimidin-4-yl)oxy]piperidine-1-carboxylate at room temperature and stirred for 2 hours. The reaction was concentrated under reduced pressure and the residue was purified by reverse phase chromatography (5-50% acetonitrile in water+0.05% TFA) to yield N-[3-methyl-5-(pyridin-3-yl)phenyl]-4-(piperidin-4-yloxy)pyrimidin-2-amine as a TFA salt. MS APCI calc'd for C21H24N5O [M+H]+ 362. found 362. 1H NMR (500 MHz, DMSO-d6) δ 9.67 (s, 1H), 8.91 (s, 1H), 8.65 (d, J=3.7 Hz, 1H), 8.47 (s, 2H), 8.25 (d, J=5.7 Hz, 1H), 8.19 (d, J=8.0 Hz, 1H), 7.87 (s, 1H), 7.71-7.61 (m, 1H), 7.59 (s, 1H), 7.17 (s, 1H), 6.31 (d, J=5.7 Hz, 1H), 5.24 (s, 1H), 3.19 (s, 2H), 2.97 (s, 2H), 2.36 (s, 2H), 2.09 (s, 3H), 1.90 (s, 2H).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customthe residue was purified by reverse phase chromatography (5-50% acetonitrile in water+0.05% TFA)

Sources & evidence

ORD record
ord-ef084d0a0e7b4efc8d50b790dea20e12
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

Loading…