Methyl 2-(1H-indazol-6-ylamino)-6-((1R,2S)-2-aminocyclohexylamino)-4-cyanonicotinate → 4-(1H-Indazol-6-ylamino)-6-((1R,2S)-2-aminocyclohexylamino)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one

HRID 515985Notes

Reaction equation

HRID 515985 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:10][C:11]3[N:20]=[C:19]([NH:21][C@@H:22]4[CH2:27][CH2:26][CH2:25][CH2:24][C@@H:23]4[NH2:28])[CH:18]=[C:17]([C:29]#[N:30])[C:12]=3[C:13](OC)=[O:14])[CH:8]=2)[CH:3]=[N:2]1>CO.[Pd]>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:10][C:11]3[C:12]4[C:13](=[O:14])[NH:30][CH2:29][C:17]=4[CH:18]=[C:19]([NH:21][C@@H:22]4[CH2:27][CH2:26][CH2:25][CH2:24][C@@H:23]4[NH2:28])[N:20]=3)[CH:8]=2)[CH:3]=[N:2]1

Participants

4

Reactant 1

HCID 58317648Methyl 2-(1H-indazol-6-ylamino)-6-((1R,2S)-2-aminocyclohexylamino)-4-cyanonicotinate

Product 1

HCID 532521134-(1H-Indazol-6-ylamino)-6-((1R,2S)-2-aminocyclohexylamino)-1H-pyrrolo[3,4-c]pyridin-3(2H)-oneYield 18.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 2-(1H-indazol-6-ylamino)-6-((1R,2S)-2-aminocyclohexylamino)-4-cyanonicotinate (88 mg, 218 mmol) in MeOH (2 mL) was added palladium on carbon, and the resulting mixture was stirred at room temperature overnight under H2 atmosphere. The mixture was subsequently filtered to remove the catalyst and the filtrate was evaporated. The residue was diluted with saturated aq NaHCO3 and MeOH, and the mixture was stirred at RT for 30 min. The resulting suspension was filtered and the precipitate was washed with EtOAc and dried to give the title compound as a white solid (15 mg, 18.2%). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.22-1.74 (m, 8 H), 3.13 (br s, 1H), 3.94-4.07 (m, 1 H), 4.21 (s, 2 H), 6.02-6.14 (m, 1 H), 6.70 (br s, 1 H), 7.13 (d, J=8.30 Hz, 1 H), 7.63 (d, J=8.30 Hz, 1 H), 7.94 (d, J=2.93 Hz, 2 H), 8.23 (s, 1 H), 9.08 (s, 1 H), 12.84 (br s, 1 H). [M+H] calc'd for C20H23N7O, 378; found, 378.

Workup

  1. filtrationThe mixture was subsequently filtered
  2. customto remove the catalyst
  3. customthe filtrate was evaporated
  4. additionThe residue was diluted with saturated aq NaHCO3 and MeOH
  5. stirringthe mixture was stirred at RT for 30 min
  6. filtrationThe resulting suspension was filtered
  7. washthe precipitate was washed with EtOAc
  8. customdried

Sources & evidence

ORD record
ord-76bffa252a9c408684544cdf72670927
Source dataset
uspto-grants-2015_08
Patent number
US09108970B2

Reaction notes

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