Trifluoroacetic acid → (+/-)-3-(N-methyl-4-(1-(6-(4-phenyl-1H-pyrazol-1-yl)pyridin-3-ylamino)butyl)benzamido)propanoic acid

HRID 537569Notes

Reaction equation

HRID 537569 reaction equation
[CH3:1][N:2]([CH2:33][CH2:34][C:35]([O:37]C(C)(C)C)=[O:36])[C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([NH:14][C:15]2[CH:16]=[N:17][C:18]([N:21]3[CH:25]=[C:24]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH:23]=[N:22]3)=[CH:19][CH:20]=2)[CH2:11][CH2:12][CH3:13])=[CH:6][CH:5]=1.C(O)(C(F)(F)F)=O>CC#N>[CH3:1][N:2]([CH2:33][CH2:34][C:35]([OH:37])=[O:36])[C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([NH:14][C:15]2[CH:16]=[N:17][C:18]([N:21]3[CH:25]=[C:24]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:23]=[N:22]3)=[CH:19][CH:20]=2)[CH2:11][CH2:12][CH3:13])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68178655(+/-)-tert-butyl 3-(N-methyl-4-(1-(6-(4-phenyl-1H-pyrazol-1-yl)pyridin-3-ylamino)butyl)benzamido)propanoate

Product 1

HCID 68156477(+/-)-3-(N-methyl-4-(1-(6-(4-phenyl-1H-pyrazol-1-yl)pyridin-3-ylamino)butyl)benzamido)propanoic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent3×

Procedure

The title compound was prepared by a method analogous to that described in Step C of Example 1, using (+/−)-tert-butyl 3-(N-methyl-4-(1-(6-(4-phenyl-1H-pyrazol-1-yl)pyridin-3-ylamino)butyl)benzamido)propanoate. Column: Waters Atlantis dC18 4.6×50 mm, 5 μm. Modifier: TFA 0.05%. Gradient: 95% H20/5% MeCN linear to 5% H20/95% MeCN over 4.0 min, Hold at 5% H20/95% MeCN to 5.0 min. Flow: 2.0 mL/min. Retention time: 3.27 min. MS (M+1): 498.1.

Workup

  1. customto 5.0 min

Sources & evidence

ORD record
ord-72e44d0f801445afa25bcc3191da6b18
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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