Trifluoroacetic acid → HCID 89995628, compound

HRID 523050Notes

Reaction equation

HRID 523050 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[N:15]=[CH:16][C:17]4[C:22]([CH:23]=3)=[CH:21][C:20]([C:24]3[CH:25]=[N:26][N:27]([CH:29]5[CH2:34][CH2:33][N:32](C(OC(C)(C)C)=O)[CH2:31][CH2:30]5)[CH:28]=3)=[CH:19][CH:18]=4)=[C:9]([O:42][CH3:43])[CH:8]=2)=[CH:5][N:4]=[C:3]1[CH3:44].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[N:15]=[CH:16][C:17]4[C:22]([CH:23]=3)=[CH:21][C:20]([C:24]3[CH:25]=[N:26][N:27]([CH:29]5[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]5)[CH:28]=3)=[CH:19][CH:18]=4)=[C:9]([O:42][CH3:43])[CH:8]=2)=[CH:5][N:4]=[C:3]1[CH3:44]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 73388856HCID 73388856, compound

Product 1

HCID 89995628HCID 89995628, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(4-(3-((4-(1,2-dimethyl-1H-imidazol-5-yl)-2-methoxyphenyl)-amino)isoquinolin-6-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate (Example 4, 27 mg, 0.045 mmol) in DCM (6 mL) at 0° C. was added TFA (0.6 mL) and the reaction was stirred at room temperature for 4 hours. The solvents were removed in vacuo and the residue was purified by SCX-2 column eluting with 2M NH3/MeOH to afford the title compound as a yellow oil (19 mg, 85%).

Workup

  1. customThe solvents were removed in vacuo
  2. customthe residue was purified by SCX-2 column
  3. washeluting with 2M NH3/MeOH

Sources & evidence

ORD record
ord-a080e41434bc4223b6c79e989d69c13b
Source dataset
uspto-grants-2016_05
Patent number
US09334286B2

Reaction notes

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