Trifluoroacetic acid → Ammonium Hydroxide

HRID 453157Notes

Reaction equation

HRID 453157 reaction equation
C([O:5]C([N:8]1[CH:17]([CH3:18])[CH2:16][C:15]2[C:14]([O:19][C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[N:25]([C:29](=[O:40])[NH:30][C:31]3[NH:32][N:33]=[C:34]([C:36]([CH3:39])([CH3:38])[CH3:37])[CH:35]=3)[CH:24]=[CH:23]4)=[N:13][CH:12]=[N:11][C:10]=2[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH4+:8].[OH-:5].[C:36]([C:34]1[CH:35]=[C:31]([NH:30][C:29]([N:25]2[C:26]3[C:22](=[CH:21][C:20]([O:19][C:14]4[C:15]5[CH2:16][CH:17]([CH3:18])[NH:8][CH2:9][C:10]=5[N:11]=[CH:12][N:13]=4)=[CH:28][CH:27]=3)[CH:23]=[CH:24]2)=[O:40])[NH:32][N:33]=1)([CH3:39])([CH3:37])[CH3:38]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178422188HCID 178422188, compound

Product 2

HCID 14923Ammonium HydroxideYield 0.1%HCID 178422187HCID 178422187, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-[1-(5-tert-butyl-2H-pyrazol-3-ylcarbamoyl)-1H-indol-5-yloxy]-6-methyl-5,8-dihydro-6H-pyrido[3,4-d]pyrimidine-7-carboxylic acid tert-butyl ester (300 mg, 0.55 mmol), DCM (5 mL), and TFA (5 mL) is stirred at rt for 2 h. At that point the solution is concentrated and the residue separated via semi-prep HPLC(C18; 10-100% I/H2O with 0.1% NH4OH) to give the title compound.

Workup

  1. concentrationAt that point the solution is concentrated
  2. customthe residue separated via semi-prep HPLC(C18

Sources & evidence

ORD record
ord-f24d3aba71b14574b0b4687ecb65b030
Source dataset
uspto-grants-2013_07
Patent number
US08492393B2

Reaction notes

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