Trifluoroacetic acid → HCID 73386774, compound

HRID 1480763Notes

Reaction equation

HRID 1480763 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([N:11]2[CH2:14][CH:13]([O:15][CH3:16])[CH2:12]2)=[O:10])[CH:6]=[CH:5][C:4]=1[NH:17][C:18]1[N:19]=[CH:20][C:21]2[C:26]([CH:27]=1)=[C:25]([C:28]1[CH:29]=[N:30][N:31]([CH:33]3[CH2:38][CH2:37][N:36](C(OC(C)(C)C)=O)[CH2:35][CH2:34]3)[CH:32]=1)[CH:24]=[CH:23][CH:22]=2.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([N:11]2[CH2:12][CH:13]([O:15][CH3:16])[CH2:14]2)=[O:10])[CH:6]=[CH:5][C:4]=1[NH:17][C:18]1[N:19]=[CH:20][C:21]2[C:26]([CH:27]=1)=[C:25]([C:28]1[CH:29]=[N:30][N:31]([CH:33]3[CH2:34][CH2:35][NH:36][CH2:37][CH2:38]3)[CH:32]=1)[CH:24]=[CH:23][CH:22]=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 73386772HCID 73386772, compound

Product 1

HCID 73386774HCID 73386774, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(4-(3-((2-methoxy-4-(3-methoxyazetidine-1-carbonyl)phenyl)-amino)isoquinolin-5-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate (Example 3, 23 mg, 0.038 mmol) in DCM (8 mL) at 0° C. was added TFA (0.5 mL). The reaction was stirred at room temperature for 16 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 yellow oil (19 mg, 98%).

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-fe4d90545b1e477394a67b06b985b52e
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

Loading…