Trifluoroacetic acid → 3-((3-((2-(6-((3-Methylbenzyl)amino)pyrimidin-4-yl)-4-(piperidin-1-yl)-phenyl)carbamoyl)benzyl)thio)propanoic acid

HRID 1407968Notes

Reaction equation

HRID 1407968 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:45]=[CH:46][CH:47]=1)[CH2:5][NH:6][C:7]1[N:12]=[CH:11][N:10]=[C:9]([C:13]2[CH:18]=[C:17]([N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:16]=[CH:15][C:14]=2[NH:25][C:26]([C:28]2[CH:29]=[C:30]([CH:42]=[CH:43][CH:44]=2)[CH2:31][S:32][CH2:33][CH2:34][C:35]([O:37]C(C)(C)C)=[O:36])=[O:27])[CH:8]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][C:2]1[CH:3]=[C:4]([CH:45]=[CH:46][CH:47]=1)[CH2:5][NH:6][C:7]1[N:12]=[CH:11][N:10]=[C:9]([C:13]2[CH:18]=[C:17]([N:19]3[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]3)[CH:16]=[CH:15][C:14]=2[NH:25][C:26]([C:28]2[CH:29]=[C:30]([CH:42]=[CH:43][CH:44]=2)[CH2:31][S:32][CH2:33][CH2:34][C:35]([OH:37])=[O:36])=[O:27])[CH:8]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66586810Tert-butyl 3-(3-(2-(6-(3-methylbenzylamino)pyrimidin-4-yl)-4-(piperidin-1-yl)phenylcarbamoyl)benzylthio)propanoate

Product 1

HCID 665869673-((3-((2-(6-((3-Methylbenzyl)amino)pyrimidin-4-yl)-4-(piperidin-1-yl)-phenyl)carbamoyl)benzyl)thio)propanoic acidYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 100-mL round-bottom flask, was placed a solution of tert-butyl 3-(3-(2-(6-(3-methylbenzylamino)pyrimidin-4-yl)-4-(piperidin-1-yl)phenylcarbamoyl)benzylthio)propanoate (180 mg, 0.28 mmol, 1.00 equiv) in dichloromethane (5 mL), and 2,2,2-trifluoroacetic acid (2 mL). The resulting solution was stirred for 3 h at room temperature. The resulting mixture was concentrated under vacuum. The crude product was purified by reverse phase HPLC eluting with a water/CH3CN gradient containing 0.05% TFA. The product was obtained as 84 mg (51%) of a yellow solid. 1H-NMR (300 MHz, DMSO-d6, ppm): δ 9.42 (s, 1H), 8.84 (s, 1H), 7.80 (s, 1H), 7.71 (m, 2H), 7.52 (m, 1H), 7.45 (m, 1H), 7.24 (m, 6H), 6.90 (s, 1H), 5.42 (s, 2H), 4.64 (m, 1H), 3.82 (s, 2H), 3.26 (m, 4H), 2.59 (m, 2H), 1.67 (m, 6H). MS (ES, m/z): 596 [M+H]+.

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. customThe crude product was purified by reverse phase HPLC
  4. washeluting with a water/CH3CN gradient
  5. additioncontaining 0.05% TFA

Sources & evidence

ORD record
ord-bd330b41ea6e459dac8c5d34d2e61b58
Source dataset
uspto-grants-2014_12
Patent number
US08916569B2

Reaction notes

Loading…