Methyl chloroformate → HCID 15908294, compound

HRID 2270099Notes

Reaction equation

HRID 2270099 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=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:35](Cl)(=[O:38])[O:36][CH3:37]>C(Cl)Cl>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=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:35]([O:36][CH3:37])=[O:38])[CH2:24]2)[CH:13]=1)=[O:11]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 20714284HCID 20714284, compound

Product 1

HCID 15908294HCID 15908294, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Then, to a 4 ml anhydrous methylene chloride solution of (S)-N-(2,6-dichlorophenyl)-1-(3-pyrrolidyl)-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide, 28 μl (0.20 mmol) of triethylamine and 12.4 μl (0.16 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=1/2) to obtain 55 mg (67%) 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=1/2)

Sources & evidence

ORD record
ord-fa95401d35384a9684172e77cd20907d
Source dataset
uspto-grants-2001_12
Patent number
US06331548B1

Reaction notes

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