Methyl chloroformate → HCID 178502079, compound

HRID 1971457Notes

Reaction equation

HRID 1971457 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[N:5]=[C:6]([NH:9][C:10]([NH:12][CH2:13][C:14]2[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[CH:16][C:15]=2[O:22][CH3:23])=[NH:11])[S:7][CH:8]=1.CN1CCOCC1.[CH3:31][O:32][C:33](Cl)=[O:34]>C1COCC1>[CH3:31][O:32][C:33](=[O:34])[NH:2][CH2:3][C:4]1[N:5]=[C:6]([NH:9][C:10]([NH:12][CH2:13][C:14]2[C:15]([O:22][CH3:23])=[CH:16][CH:17]=[CH:18][C:19]=2[O:20][CH3:21])=[NH:11])[S:7][CH:8]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 79724-MethylmorpholineHCID 178491368HCID 178491368, compound

Product 1

HCID 178502079HCID 178502079, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 360 mg (1.12 mmol) N-[4-(aminomethyl)-1,3-thiazole-2-yl]-N′-(2,6-dimethoxybenzyl)guanidine hydrochloride, Example 154 free base, in 13.5 ml THF were added 0.2 ml NMM, and 0.1 ml chloroformic acid methyl ester in 1.5 ml THF were added drop-wise with stirring. Following completion of the reaction, the mixture was concentrated, was diluted with dichloromethane, was washed with saturated NaCl solution, was dried and was concentrated. Chromatography of the crude product on silica gel (dichloromethane/methanol 0-1%) yielded 140 mg; ESI-MS [M+H+]=380.05.

Workup

  1. additionwere added drop-wise
  2. customcompletion of the reaction
  3. concentrationthe mixture was concentrated
  4. additionwas diluted with dichloromethane
  5. washwas washed with saturated NaCl solution
  6. customwas dried
  7. concentrationwas concentrated

Sources & evidence

ORD record
ord-9a060b1370dc431fb8f442282590d2bf
Source dataset
uspto-grants-2013_04
Patent number
US08431604B2

Reaction notes

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