Trifluoroacetic acid → HCID 77846918, compound

HRID 509081Notes

Reaction equation

HRID 509081 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[N:12]=[CH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[C:16]([N:21]1[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]1)[CH:15]=2)=[O:10].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[N:12]=[CH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[C:16]([N:21]1[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]1)[CH:15]=2)=[O:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86731460HCID 86731460, compound

Product 1

HCID 77846918HCID 77846918, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(3-(2-aminophenylcarbamoyl)isoquinolin-7-yl)piperazine-1-carboxylate (100 mg, 0.22 mmol) in DCM (3 mL) was added TFA (1.5 mL). The resulting mixture was stirred at r.t. for 1 h. The mixture was concentrated to a residue, which was purified by Pre-HPLC to afford the desired compound, N-(2-aminophenyl)-7-(piperazin-1-yl)isoquinoline-3-carboxamide (75 mg, 70%) as a light yellow solid. 1H NMR (500 MHz, DMSO) δ 10.12 (s, 1H), 9.18 (s, 1H), 8.48 (s, 1H), 8.03 (d, J=9.1 Hz, 1H), 7.73 (d, J=7.0 Hz, 1H), 7.61 (d, J=7.9 Hz, 1H), 7.45 (s, 1H), 6.95 (t, J=7.6 Hz, 1H), 6.85 (d, J=7.8 Hz, 1H), 6.68 (t, J=7.5 Hz, 1H), 4.89 (s, 2H), 3.33-3.12 (m, 4H), 2.93-2.84 (m, 4H). LCMS: 1.69 min, m/z=348 (M+H)+

Workup

  1. concentrationThe mixture was concentrated to a residue, which
  2. customwas purified by Pre-HPLC

Sources & evidence

ORD record
ord-4757894a589146629d2b40c4acdfc3ac
Source dataset
uspto-grants-2015_08
Patent number
US09096549B2

Reaction notes

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