Methanol → HCID 22181137, compound

HRID 1796212Notes

Reaction equation

HRID 1796212 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][CH2:22]/[CH:23]=[CH:24]/[C:25]3[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=3)[C:28]#[N:29])=[CH:17][C:16]=2[C:33](=[O:35])[NH2:34])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:36]([S:38](Cl)(=[O:40])=[O:39])[CH3:37].N1C=CC=CC=1.CO>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]([CH2:22]/[CH:23]=[CH:24]/[C:25]3[CH:32]=[CH:31][CH:30]=[C:27]([C:28]#[N:29])[CH:26]=3)[S:38]([CH2:36][CH3:37])(=[O:40])=[O:39])=[CH:17][C:16]=2[C:33](=[O:35])[NH2:34])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 1049Pyridine2×HCID 11667Ethanesulfonyl chloride2×HCID 22181014HCID 22181014, compound

Product 1

HCID 22181137HCID 22181137, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3-[3-[N-[4-(1-t-butoxycarbonylpiperidin-4-yloxy)-3-carbamoylphenyl]amino]-1-(E)-propenyl]benzonitrile (0.92 g) obtained in reference example 130 in dichloromethane (15 ml) were successively added dropwise ethanesulfonyl chloride (0.22 ml) and pyridine (0.31 ml) with stirring under ice-cooling, and the resulting mixture was stirred at room temperature overnight. At the end of this time, to the reaction mixture were furthermore added dropwise ethanesulfonyl chloride (0.04 ml) and pyridine (0.16 ml) with stirring under ice-cooling, and the resulting mixture was stirred at room temperature for 5 hours. After stirring, to the reaction mixture was added methanol (3 ml), and the resulting mixture was evaporated in vacuo. The residue obtained was purified by chromatography on a silica gel column using a mixed solvent of dichloromethane and methanol (10:0˜9:1) as the eluent to afford the title compound (1.08 g, yield: 90%) as a yellow oil.

Workup

  1. temperaturecooling
  2. stirringthe resulting mixture was stirred at room temperature overnight
  3. stirringwith stirring under ice-
  4. temperaturecooling
  5. stirringthe resulting mixture was stirred at room temperature for 5 hours
  6. stirringAfter stirring, to the reaction mixture
  7. customthe resulting mixture was evaporated in vacuo
  8. customThe residue obtained
  9. customwas purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-8d57ce8f83ff4760aa4de538699240c8
Source dataset
uspto-grants-2006_04
Patent number
US07030138B2

Reaction notes

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