Trifluoroacetic acid → 6-((1R,2S)-2-Aminocyclohexylamino)-4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one

HRID 515997Notes

Reaction equation

HRID 515997 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[C:12]3[C:13](=[O:16])[NH:14][CH2:15][C:11]=3[CH:10]=[C:9]([NH:17][C@@H:18]3[CH2:23][CH2:22][CH2:21][CH2:20][C@@H:19]3[NH:24]C(=O)OC(C)(C)C)[N:8]=2)[CH:4]=[N:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:24][C@H:19]1[CH2:20][CH2:21][CH2:22][CH2:23][C@H:18]1[NH:17][C:9]1[N:8]=[C:7]([C:5]2[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=2)[C:12]2[C:13](=[O:16])[NH:14][CH2:15][C:11]=2[CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86654709tert-Butyl (1S,2R)-2-(4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate

Product 1

HCID 532522756-((1R,2S)-2-Aminocyclohexylamino)-4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-oneYield 14%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl (1S,2R)-2-(4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate (94 mg, 0.22 mmol) and TFA (1 mL, 12.98 mmol) in DCM (1 mL) was stirred at RT for 2 h. The mixture was subsequently concentrated. The residue was purified by preparative HPLC (01-25; 5.45 min) and basified to give the title compound as a yellow solid (10 mg, 14%). 1H NMR (500 MHz, DMSO-d6) δ ppm 122-1.61 (m, 8 H), 3.63 (s, 3 H), 4.19 (s, 2 H), 6.46 (br s, 1 H), 7.98 (s, 1 H), 8.29 (s, 1 H), 8.85 (s, 1 H). [M+H] calc'd for C17H22N6O, 327; found, 327.

Workup

  1. concentrationThe mixture was subsequently concentrated
  2. customThe residue was purified by preparative HPLC (01-25; 5.45 min)

Sources & evidence

ORD record
ord-58868ff665a849409462fe623e1ea31f
Source dataset
uspto-grants-2015_08
Patent number
US09108970B2

Reaction notes

Loading…