Chloroform → HCID 59398179, compound

HRID 2193322Notes

Reaction equation

HRID 2193322 reaction equation
C(Cl)(Cl)Cl.[C:5]([O:9][C:10](=[O:43])[N:11]([CH2:32][C:33]1[CH:42]=[CH:41][C:36]2[O:37][CH2:38][CH2:39][O:40][C:35]=2[CH:34]=1)[CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][N:20]2[C:29]3[C:24](=[C:25]([NH2:30])[CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][C:21]2=[O:31])[CH2:14][CH2:13]1)([CH3:8])([CH3:7])[CH3:6].Cl[C:45]([O:47][CH3:48])=[O:46]>C(N(CC)CC)C>[CH3:48][O:47][C:45](=[O:46])[NH:30][C:25]1[CH:26]=[CH:27][CH:28]=[C:29]2[C:24]=1[CH:23]=[CH:22][C:21](=[O:31])[N:20]2[CH2:19][CH2:18][N:15]1[CH2:14][CH2:13][CH:12]([N:11]([C:10]([O:9][C:5]([CH3:8])([CH3:6])[CH3:7])=[O:43])[CH2:32][C:33]2[CH:42]=[CH:41][C:36]3[O:37][CH2:38][CH2:39][O:40][C:35]=3[CH:34]=2)[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 6586Methyl chloroformate2×HCID 59397938HCID 59397938, compound

Product 1

HCID 59398179HCID 59398179, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent2×

Procedure

To 2 mL of a chloroform solution containing 80 mg of tert-butyl(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(5-amino-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate, 45 mg of triethylamine and 42 mg of methyl chloroformate were added, and stirred at room temperature for 3 days. To the reaction mixture, 225 mg of triethylamine and 210 mg of methyl chloroformate were added, and stirred at room temperature overnight. The reaction mixture was purified by silica gel column chromatography [Silica Gel; Fuji Silysia Chemical Ltd., Chromatorex-NH, eluent; hexane:ethyl acetate=1:4], to give 40 mg of N-(1-(2-(4-((tert-butoxycarbonyl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-2-oxo-1,2-dihydroquinolin-5-yl)carbamic acid methyl ester as a pale yellow oil.

Workup

  1. additionwere added
  2. stirringstirred at room temperature overnight
  3. customThe reaction mixture was purified by silica gel column chromatography [Silica Gel; Fuji Silysia Chemical Ltd., Chromatorex-NH, eluent; hexane:ethyl acetate=1:4]

Sources & evidence

ORD record
ord-058724b61c6945f2818d816932fd8e40
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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