Chloroform → HCID 59398068, compound

HRID 2193318Notes

Reaction equation

HRID 2193318 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].[CH2:44]([N:46]=[C:47]=[O:48])[CH3:45]>C(N(CC)CC)C>[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[CH2:13][CH2:14][N:15]([CH2:18][CH2:19][N:20]2[C:29]3[C:24](=[C:25]([NH:30][C:47]([NH:46][CH2:44][CH3:45])=[O:48])[CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][C:21]2=[O:31])[CH2:16][CH2:17]1)([CH3:8])([CH3:6])[CH3:7]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 8022Ethyl isocyanateHCID 59397938HCID 59397938, compound

Product 1

HCID 59398068HCID 59398068, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

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 31 mg of ethyl isocyanate were added, and stirred at room temperature for 3 days. The reaction mixture was purified by silica gel column chromatography [Silica Gel; Fuji Silysia Chemical Ltd., Chromatorex-NH, eluent; ethyl acetate:methanol=10:1], to give 60 mg of tert-butyl(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(5-(3-ethylureido)-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate as a yellow oil.

Workup

  1. additionwere added
  2. customThe reaction mixture was purified by silica gel column chromatography [Silica Gel; Fuji Silysia Chemical Ltd., Chromatorex-NH, eluent; ethyl acetate:methanol=10:1]

Sources & evidence

ORD record
ord-beda966e90464dfab08715c60c5ad31e
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

Loading…