Acetic Acid → tert-Butyl (1S,2R)-2-(4-(1-ethyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate

HRID 2092821Notes

Reaction equation

HRID 2092821 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[NH:15][C:16]1[CH:25]=[C:24]([C:26]#[N:27])[C:19]([C:20]([O:22]C)=O)=[C:18]([C:28]2[CH:29]=[N:30][N:31]([CH2:33][CH3:34])[CH:32]=2)[N:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(O)=O.C(=O)([O-])[O-].[K+].[K+]>CO.[Pd].C(Cl)Cl>[CH2:33]([N:31]1[CH:32]=[C:28]([C:18]2[C:19]3[C:20](=[O:22])[NH:27][CH2:26][C:24]=3[CH:25]=[C:16]([NH:15][C@@H:10]3[CH2:11][CH2:12][CH2:13][CH2:14][C@@H:9]3[NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[N:17]=2)[CH:29]=[N:30]1)[CH3:34]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 67237978Methyl 6-((1R,2S)-2-(tert-butoxycarbonylamino)cyclohexylamino)-4-cyano-2-(1-ethyl-1H-pyrazol-4-yl)nicotinate

Product 1

HCID 86654724tert-Butyl (1S,2R)-2-(4-(1-ethyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamateYield 86%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a flask containing methyl 6-((1R,2S)-2-(tert-butoxycarbonylamino)cyclohexyl-amino)-4-cyano-2-(1-ethyl-1H-pyrazol-4-yl)nicotinate (62 mg, 0.132 mmol) in MeOH (2 mL) was added HOAc (1 mL) to give a yellow solution. Palladium on carbon was added (14.08 mg, 0.132 mmol). The flask was evacuated and filled with H2 three times, after which the mixture was stirred vigorously at RT under a H2 atmosphere overnight. The mixture was filtered through Celite, and the solvent was removed in vacuo to give a residue, which was dissolved in DCM (10 mL) and MeOH (10 mL). Potassium carbonate was added and the mixture was stirred for 5 h. The solids were filtered out and the filtrate concentrated to give the title compound (50 mg, 86%). [M+H] calc'd for C23H32N6O3, 441. found, 441.

Workup

  1. customto give a yellow solution
  2. customThe flask was evacuated
  3. additionfilled with H2 three times
  4. filtrationThe mixture was filtered through Celite
  5. customthe solvent was removed in vacuo
  6. customto give a residue, which
  7. stirringthe mixture was stirred for 5 h
  8. filtrationThe solids were filtered out
  9. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-8ff33255fa0b4a0eada06f13671d1e8b
Source dataset
uspto-grants-2013_05
Patent number
US08440689B2

Reaction notes

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