Carbamate → HCID 68752163, compound

HRID 624290Notes

Reaction equation

HRID 624290 reaction equation
[NH2:1][C:2]1[N:7]=[N:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:18](Cl)(=O)[O:19]C1C=CC([N+]([O-])=O)=CC=1.Cl.Cl.[CH2:33]1[C:41]2[CH:40]=[CH:39][N:38]=[CH:37][C:36]=2[CH2:35][NH:34]1.C(C(C(C)C)(C(C)C)CN)(C)C.C(=O)([O-])N>ClCCl.CN(C)C=O>[CH2:33]1[C:41]2[CH:40]=[CH:39][N:38]=[CH:37][C:36]=2[CH2:35][N:34]1[C:18]([NH:1][C:2]1[N:7]=[N:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1)=[O:19]

Participants

9

Reactant 6

HCID 276CarbamateHCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 437068HCID 437068, compoundHCID 14536428Methyl 6-aminopyridazine-3-carboxylateHCID 189536442,3-Dihydro-1H-pyrrolo[3,4-c]pyridine--hydrogen chloride (1/2)

Product 1

HCID 68752163HCID 68752163, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

Methyl 6-aminopyridazine-3-carboxylate (2 g, 13.06 mmol) was suspended in dichloromethane (50 ml) followed by addition of dry pyridine (1.265 ml, 15.67 mmol) under nitrogen. To this suspension was added a dichloromethane solution of 4-nitrophenyl carbonochloridate (2.99 g, 14.37 mmol) via syringe at ambient temperature. The mixture was stirred overnight to give a suspension that was concentrated to half volume under a stream of nitrogen. 2,3-Dihydro-1H-pyrrolo[3,4-c]pyridine, dihydrochloride (2.52 g, 13.06 mmol) was dissolved in 30 ml dimethylformamide with triisopropylethylamine (6.84 ml, 39.2 mmol) and added to the carbamate mixture via syringe. After stirring the mixture overnight and removing most of the solvent under vacuum, water was added; and the resulting suspension was stirred for 30 minutes and filtered to give a solid which was washed with water. Flash chromatography of the dried solid gave the title compound.

Workup

  1. customto give a suspension that
  2. concentrationwas concentrated to half volume under a stream of nitrogen
  3. stirringAfter stirring the mixture overnight
  4. customremoving most of the solvent under vacuum, water
  5. additionwas added
  6. stirringand the resulting suspension was stirred for 30 minutes
  7. filtrationfiltered
  8. customto give a solid which
  9. washwas washed with water

Sources & evidence

ORD record
ord-ebb8fbd01e77457496f72ccdaebf6325
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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