Methyl chloroformate → Methyl 2-[(2-aminophenyl)carbamoyl]-6,7-dihydro[1,3]thiazolo[5,4-c]pyridine-5(4H)-carboxylate

HRID 2093073Notes

Reaction equation

HRID 2093073 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14]([C:16]1[S:17][C:18]2[CH2:19][NH:20][CH2:21][CH2:22][C:23]=2[N:24]=1)=[O:15]>CN(C=O)C>[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14]([C:16]1[S:17][C:18]2[CH2:19][N:20]([C:2]([O:4][CH3:5])=[O:3])[CH2:21][CH2:22][C:23]=2[N:24]=1)=[O:15]

Participants

4

Reactant 2

HCID 6586Methyl chloroformateHCID 58117006N-(2-aminophenyl)-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxamide

Product 1

HCID 66863865Methyl 2-[(2-aminophenyl)carbamoyl]-6,7-dihydro[1,3]thiazolo[5,4-c]pyridine-5(4H)-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl chloroformate (1.0 mmol) was added drop wise to N-(2-aminophenyl)-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxamide obtained from step VIII of example 1 (1.0 mmol) solution in 10 mL of dry DMF at 0° C. Reaction mixture was stirred for additional 3 h Reaction mixture was concentrated, diluted with water, extracted with dichloromethane, washed with brine solution, and dried over anhydrous Na2SO4. Concentrated and purified by column chromatography to get the title compound.

Workup

  1. customReaction mixture
  2. customReaction mixture
  3. concentrationwas concentrated
  4. additiondiluted with water
  5. extractionextracted with dichloromethane
  6. washwashed with brine solution
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationConcentrated
  9. custompurified by column chromatography

Sources & evidence

ORD record
ord-decfa76235244bf9aed15056c76c6f41
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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