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Trifluoroacetic acid → 3-(3-((2-(4-((4-(1H-pyrazol-1-yl)benzyl)carbamoyl)pyridin-2-yl)-4-(piperidin-1-yl)phenyl)carbamoyl)benzylthio)propanoic acid

HRID 1408162
Notes
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Reaction equation

HRID 1408162 reaction equation
[N:1]1([C:6]2[CH:53]=[CH:52][C:9]([CH2:10][NH:11][C:12]([C:14]3[CH:19]=[CH:18][N:17]=[C:16]([C:20]4[CH:25]=[C:24]([N:26]5[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]5)[CH:23]=[CH:22][C:21]=4[NH:32][C:33]([C:35]4[CH:36]=[C:37]([CH:49]=[CH:50][CH:51]=4)[CH2:38][S:39][CH2:40][CH2:41][C:42]([O:44]C(C)(C)C)=[O:43])=[O:34])[CH:15]=3)=[O:13])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([CH2:10][NH:11][C:12]([C:14]3[CH:19]=[CH:18][N:17]=[C:16]([C:20]4[CH:25]=[C:24]([N:26]5[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]5)[CH:23]=[CH:22][C:21]=4[NH:32][C:33]([C:35]4[CH:36]=[C:37]([CH:49]=[CH:50][CH:51]=4)[CH2:38][S:39][CH2:40][CH2:41][C:42]([OH:44])=[O:43])=[O:34])[CH:15]=3)=[O:13])=[CH:52][CH:53]=2)[CH:5]=[CH:4][CH:3]=[N:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 66587472tert-butyl 3-(3-((2-(4-((4-(1H-pyrazol-1-yl)benzyl)carbamoyl)pyridin-2-yl)-4-(piperidin-1-yl)phenyl)carbamoyl)benzylthio)propanoate

Product 1

HCID 696314883-(3-((2-(4-((4-(1H-pyrazol-1-yl)benzyl)carbamoyl)pyridin-2-yl)-4-(piperidin-1-yl)phenyl)carbamoyl)benzylthio)propanoic acidYield 72%

Reagents, catalysts & solvents

1
HCID 6344DichloromethaneSolvent2×

Procedure

Into a 50-mL 3-necked round bottom flask, was placed tert-butyl 3-(3-((2-(4-((4-(1H-pyrazol-1-yl)benzyl)carbamoyl)pyridin-2-yl)-4-(piperidin-1-yl)phenyl)carbamoyl)benzylthio)-propanoate (130 mg, 0.18 mmol, 1.00 equiv), and dichloromethane (2 mL). This was followed by dropwise addition of trifluoroacetic acid (3 mL) with stirring. The resulting solution was stirred for 60 min at room temperature. The solution was adjusted to pH 7 with sodium bicarbonate (aq). The resulting solution was diluted with 30 mL of dichloromethane and washed with 2×10 mL of H2O. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product (300 mg) was purified by reverse phase HPLC eluting with a water/CH3CN gradient containing 0.05% TFA. The product was obtained as 86.9 mg (72%) of a yellow solid. 1H-NMR: (300 MHz, DMSO-d6+D2O, ppm): δ 1.63 (m, 2H), 1.82 (m, 4H), 2.58-2.62 (m, 4H), 3.47 (t, 4H), 3.87 (s, 2H), 4.56 (d, 2H), 6.53 (s, 1H), 7.44-7.54 (m, 4H), 7.72-7.79 (m, 3H), 7.87-7.89 (m, 2H), 8.36 (s, 1H), 8.42 (s, 1H), 8.99 (d, 1H), 9.53 (s, 1H), 11.97 (s, 1H). MS (ES, m/z): 675 [M+H]+.

Workup

  1. customInto a 50-mL 3-necked round bottom flask, was placed
  2. stirringThe resulting solution was stirred for 60 min at room temperature
  3. washwashed with 2×10 mL of H2O
  4. dry with materialThe mixture was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe crude product (300 mg) was purified by reverse phase HPLC
  7. washeluting with a water/CH3CN gradient
  8. additioncontaining 0.05% TFA

Sources & evidence

ORD record
ord-60d5ec6eccb14c14b6e824a3f8f1a136
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08916569B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes