Potassium Carbonate → (R)-tert-Butyl 1-methoxy-3-(3-oxo-4-(m-tolylamino)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)propan-2-ylcarbamate

HRID 516082Notes

Reaction equation

HRID 516082 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:32][O:33][CH3:34])[CH2:10][NH:11][C:12]1[CH:21]=[C:20]([C:22]#[N:23])[C:15]([C:16]([O:18]C)=O)=[C:14]([NH:24][C:25]2[CH:26]=[C:27]([CH3:31])[CH:28]=[CH:29][CH:30]=2)[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.C(Cl)Cl.[Pt](=O)=O>[CH3:34][O:33][CH2:32][C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:10][NH:11][C:12]1[N:13]=[C:14]([NH:24][C:25]2[CH:26]=[C:27]([CH3:31])[CH:28]=[CH:29][CH:30]=2)[C:15]2[C:16](=[O:18])[NH:23][CH2:22][C:20]=2[CH:21]=1

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 67238996(R)-Methyl 6-(2-(tert-butoxycarbonylamino)-3-methoxypropylamino)-4-cyano-2-(m-tolylamino)nicotinate

Product 1

HCID 67238901(R)-tert-Butyl 1-methoxy-3-(3-oxo-4-(m-tolylamino)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)propan-2-ylcarbamate

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a round-bottomed flask was added (R)-methyl 6-(2-(tert-butoxycarbonylamino)-3-methoxypropylamino)-4-cyano-2-(m-tolylamino)nicotinate (84.5 mg, 0.180 mmol) in acetic acid (3 mL) and DCM (10 mL). To the resulting yellow solution was added platinum(IV) oxide (4.09 mg, 0.018 mmol). The flask was evacuated and back filled with hydrogen (3×1 atm). The reaction mixture was stirred vigorously at RT for 16 h, subsequently diluted with DCM (10 mL), and filtered through Celite. The filtrate was concentrated to an oil, which was diluted with DCM (10 mL). Potassium carbonate (24.87 mg, 0.180 mmol) was added and the reaction mixture was stirred at RT for 12 h. The crude reaction was diluted with DCM (10 mL), filtered through Celite, and concentrated to give the title compound as a thick yellow oil, which was used without further purification (26.5 mg, 33.4%). [M+H] calc'd for C23H31N5O4, 442; found, 442.

Workup

  1. customThe flask was evacuated
  2. additionback filled with hydrogen (3×1 atm)
  3. additionsubsequently diluted with DCM (10 mL)
  4. filtrationfiltered through Celite
  5. concentrationThe filtrate was concentrated to an oil, which
  6. additionwas diluted with DCM (10 mL)
  7. stirringthe reaction mixture was stirred at RT for 12 h
  8. customThe crude reaction
  9. filtrationfiltered through Celite
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-6354ce374ba74d49bd72ea0a1d405c23
Source dataset
uspto-grants-2015_08
Patent number
US09108970B2

Reaction notes

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