Methyl chloroformate → HCID 86745173, compound

HRID 846773Notes

Reaction equation

HRID 846773 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH:14]=[CH:13][C:12]3=[N:15][C:16](NC)=[N:17][C:11]3=[CH:10]2)=[CH:4][CH:3]=1.[C:20](Cl)(=[O:23])[O:21][CH3:22].[CH2:25]([N:27](CC)CC)C>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2[CH:14]=[CH:13][C:12]3=[N:15][C:16]([CH2:25][NH:27][C:20](=[O:23])[O:21][CH3:22])=[N:17][C:11]3=[CH:10]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 15096966HCID 15096966, compound

Product 1

HCID 86745173HCID 86745173, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3.0 parts of 5-[(4-fluorophenyl)methyl]-N-methyl-5H-imidazo[4,5-c]pyridin-2-amine, 2.4 parts of methyl carbonochloridate, 1.2 parts of N,N-diethylethanamine and 260 parts of dichloromethane was stirred for 2 days at room temperature. The reaction mixture was evaporated. The solid residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (94:6 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2-propanone, yielding 1 part of methyl [[5-[(4-fluorophenyl)methyl]-5H-imidazo[4,5-c]pyridin-2-yl]methyl]carbamate; mp. 178.8° C. (intermediate 98).

Workup

  1. customThe reaction mixture was evaporated
  2. customThe solid residue was purified by column-chromatography over silica gel using
  3. additiona mixture of trichloromethane and methanol (94:6 by volume) as eluent
  4. customThe pure fractions were collected
  5. customthe eluent was evaporated
  6. customThe residue was crystallized from 2-propanone

Sources & evidence

ORD record
ord-a696cd70cd0045d7a3d6afec0067f690
Source dataset
uspto-grants-1992_08
Patent number
US05137896

Reaction notes

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