Methyl chloroformate → HCID 15908297, compound

HRID 2270101Notes

Reaction equation

HRID 2270101 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[N:5][CH:6]=[C:7]([Cl:28])[C:8]=1[NH:9][C:10]([C:12]1[C:21](=[O:22])[C:20]2[C:15](=[N:16][CH:17]=[CH:18][CH:19]=2)[N:14]([C@H:23]2[CH2:27][CH2:26][NH:25][CH2:24]2)[CH:13]=1)=[O:11].C(N(CC)CC)C.[C:36](Cl)(=[O:39])[O:37][CH3:38]>C(Cl)Cl>[Cl:2][C:3]1[CH:4]=[N:5][CH:6]=[C:7]([Cl:28])[C:8]=1[NH:9][C:10]([C:12]1[C:21](=[O:22])[C:20]2[C:15](=[N:16][CH:17]=[CH:18][CH:19]=2)[N:14]([C@H:23]2[CH2:27][CH2:26][N:25]([C:36]([O:37][CH3:38])=[O:39])[CH2:24]2)[CH:13]=1)=[O:11]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 20714285HCID 20714285, compound

Product 1

HCID 15908297HCID 15908297, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Then, to a 4 ml anhydrous methylene chloride solution of (S)-N-(3,5-dichloropyridin-4-yl)-1-(3-pyrrolidyl)-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide hydrochloride, 43.6 μl (0.31 mmol) of triethylamine and 9.7 μl (0.125 mmol) of methyl chlorocarbonate were added at room temperature and stirred for 40 minutes. The reaction solution was concentrated under vacuum and the residue was purified by a silica gel chromatography (hexane/ethyl acetate=1/3) to obtain 45 mg (88%) of the above-identified compound as a colorless oily substance.

Workup

  1. concentrationThe reaction solution was concentrated under vacuum
  2. customthe residue was purified by a silica gel chromatography (hexane/ethyl acetate=1/3)

Sources & evidence

ORD record
ord-7439812c8d3147149814ebc649dace22
Source dataset
uspto-grants-2001_12
Patent number
US06331548B1

Reaction notes

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