Trifluoroacetic acid → HCID 73389347, compound

HRID 523049Notes

Reaction equation

HRID 523049 reaction equation
[OH:1][C:2]([CH3:45])([CH3:44])[CH2:3][N:4]1[CH:8]=[C:7]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[CH:15]=[N:14][C:13]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]4[N:30]5[CH2:31][CH2:32][N:33](C(OC(C)(C)C)=O)[CH2:34][C:29]5=[N:28][N:27]=4)=[CH:22][C:21]=2[O:42][CH3:43])=[CH:12]3)[CH:6]=[N:5]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:43][O:42][C:21]1[CH:22]=[C:23]([C:26]2[N:30]3[CH2:31][CH2:32][NH:33][CH2:34][C:29]3=[N:28][N:27]=2)[CH:24]=[CH:25][C:20]=1[NH:19][C:13]1[N:14]=[CH:15][C:16]2[C:11]([CH:12]=1)=[CH:10][C:9]([C:7]1[CH:6]=[N:5][N:4]([CH2:3][C:2]([CH3:45])([OH:1])[CH3:44])[CH:8]=1)=[CH:18][CH:17]=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 73389344HCID 73389344, compound

Product 1

HCID 73389347HCID 73389347, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-Butyl 3-(4-(6-(1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl)isoquinolin-3-ylamino)-3-methoxyphenyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate (Example 55, 29 mg, 0.047 mmol) in DCM (10 mL) at 0° C. was added TFA (0.35 mL). The reaction was stirred at room temperature for 16 hours before concentrating in vacuo. The residue was purified by elution through an SCX-2 column using 2M NH3/MeOH to afford the title compound as a yellow solid (17.5 mg, 72%).

Workup

  1. concentrationbefore concentrating in vacuo
  2. customThe residue was purified by elution through an SCX-2 column

Sources & evidence

ORD record
ord-0d5d1ee4b7bf498aaacb12f4a5643dbb
Source dataset
uspto-grants-2016_05
Patent number
US09334286B2

Reaction notes

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