Trifluoroacetic acid → (R)-6-(5-(2,6-difluorophenyl)-1H-indazol-3-yl)-N-(pyrrolidin-3-yl)pyrazin-2-amine

HRID 1529285Notes

Reaction equation

HRID 1529285 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14](C1CCCCO1)[N:13]=[C:12]2[C:24]1[N:29]=[C:28]([NH:30][C@@H:31]2[CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32]2)[CH:27]=[N:26][CH:25]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][N:13]=[C:12]2[C:24]1[N:29]=[C:28]([NH:30][C@@H:31]2[CH2:35][CH2:34][NH:33][CH2:32]2)[CH:27]=[N:26][CH:25]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67959703(3R)-tert-butyl 3-(6-(5-(2,6-difluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)pyrazin-2-ylamino)pyrrolidine-1-carboxylate

Product 1

HCID 67959878(R)-6-(5-(2,6-difluorophenyl)-1H-indazol-3-yl)-N-(pyrrolidin-3-yl)pyrazin-2-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3R)-tert-butyl 3-(6-(5-(2,6-difluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)pyrazin-2-ylamino)pyrrolidine-1-carboxylate (280 mg, 0.486 mmol) in DCM was added TFA (0.5 ml, 6.49 mmol). The reaction was stirred at RT for 2 h, and then TFA was removed. The residue was purified with RP-HPLC to give (R)-6-(5-(2,6-difluorophenyl)-1H-indazol-3-yl)-N-(pyrrolidin-3-yl)pyrazin-2-amine as an orange solid. MS (ESI, pos. ion) m/z: 393 (M+1); 1H NMR (400 MHz, DMSO-d6) δ ppm 8.71 (1 H, s), 8.47 (1 H, s), 7.87 (1 H, s), 7.72 (1 H, d, J=8.6 Hz), 7.41-7.55 (2 H, m), 7.18-7.31 (3 H, m), 4.22-4.36 (1 H, m), 2.88-3.05 (2 H, m), 2.61-2.82 (2 H, m), 1.97-2.12 (1 H, m), 1.57-1.73 (1 H, m).

Workup

  1. customTFA was removed
  2. customThe residue was purified with RP-HPLC

Sources & evidence

ORD record
ord-0ee076e4f9b04ee687c6d98d9b02ef08
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

Loading…