Trifluoroacetic acid → HCID 25211642, compound

HRID 2065579Notes

Reaction equation

HRID 2065579 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14](=[O:38])[NH:15][C:16]1[C:17]([CH3:37])=[N:18][CH:19]=[C:20]([NH:22][C:23]2[N:28]=[CH:27][C:26]([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)=[CH:25][N:24]=2)[CH:21]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:36][O:35][C:32]1[CH:33]=[CH:34][C:29]([C:26]2[CH:25]=[N:24][C:23]([NH:22][C:20]3[CH:21]=[C:16]([NH:15][C:14]([CH:9]4[CH2:10][CH2:11][CH2:12][CH2:13][NH:8]4)=[O:38])[C:17]([CH3:37])=[N:18][CH:19]=3)=[N:28][CH:27]=2)=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58171900HCID 58171900, compound

Product 1

HCID 25211642HCID 25211642, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-{5-[5-(4-Methoxy-phenyl)-pyrimidin-2-ylamino]-2-methyl-pyridin-3-ylcarbamoyl}-piperidine-1-carboxylic acid tert-butyl ester 20 is dissolved in DCM (1 mL) and TFA is added (2 mL). The yellow solution is stirred at rt for 2 h. The solvent and the excess of TFA are removed under vacuum and the residue is purified by preparative LCMS to afford piperidine-2-carboxylic acid {5-[5-(4-methoxy-phenyl)-pyrimidin-2-ylamino]-2-methyl-pyridin-3-yl}-amide C1. 1H NMR (400 MHz, d6-DMSO) δ 1H NMR (400 MHz, d4-CH3OH) δ 9.27 (d, J=4.0 Hz, 1H), 8.85 (d, J=4.0 Hz, 1H), 8.80 (s, 2H), 7.59-7.57 (m, 2H), 7.06-7.06 (m, 2H), 4.14 (dd, J=4.0 and 12.0 Hz, 1H), 3.86 (s, 3H), 3.52-3.48 (m, 1H), 3.15-3.12 (m, 1H), 2.62 (s, 3H), 2.45-2.44 (m, 1H), 2.07-2.06 (m, 1H), 1.98-1.95 (m, 1H), 1.89-1.85 (m, 1H), 1.79-1.75 (m, 2H). MS (m/z) (M+1)+: 419.2.

Workup

  1. customThe solvent and the excess of TFA are removed under vacuum
  2. customthe residue is purified by preparative LCMS

Sources & evidence

ORD record
ord-80ac3b467370448d8039cb87db3addba
Source dataset
uspto-grants-2012_10
Patent number
US08288540B2

Reaction notes

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