Sodium Hydroxide → HCID 178457502, compound

HRID 491800Notes

Reaction equation

HRID 491800 reaction equation
[CH:1]([NH:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]([NH:13][C:14]2[C:18]3[CH:19]=[C:20]([C:23]([O:25]C)=[O:24])[CH:21]=[CH:22][C:17]=3[O:16][C:15]=2[C:27]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][N:31]=2)=[O:28])=[O:12])[CH2:7][CH2:6]1)([CH3:3])[CH3:2].[OH-].[Na+]>O1CCCC1.CO>[C:23]([C:20]1[CH:21]=[CH:22][C:17]2[O:16][C:15]([C:27]([NH:29][C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][N:31]=3)=[O:28])=[C:14]([NH:13][C:11]([C@H:8]3[CH2:9][CH2:10][C@H:5]([NH:4][CH:1]([CH3:2])[CH3:3])[CH2:6][CH2:7]3)=[O:12])[C:18]=2[CH:19]=1)([OH:25])=[O:24]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178497417HCID 178497417, compound

Product 1

HCID 178457502HCID 178457502, compoundYield 104.6%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Trans-3-[4-(isopropylamino)cyclohexylcarbonylamino]-5-methoxycarbonyl-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide (690 mg) obtained in Example 311 is suspended in tetrahydrofuran/methanol (1:1, 10 ml), and under ice-cooling, thereto is added 4N aqueous sodium hydroxide solution (3 ml). The mixture is warmed to room temperature, and stirred for 18 hours. The reaction solution is concentrated under reduced pressure, and poured into ice-water. The mixture is neutralized with 10% hydrochloric acid, and the precipitates are collected by filtration, washed successively with water, tetrahydrofuran, and diethyl ether, and dried to give the title compound (702 mg).

Workup

  1. temperatureunder ice-cooling
  2. concentrationThe reaction solution is concentrated under reduced pressure
  3. additionpoured into ice-water
  4. filtrationthe precipitates are collected by filtration
  5. washwashed successively with water, tetrahydrofuran, and diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-476aa4da41a644cd8510a407474eddbb
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

Loading…