Sodium Hydroxide → HCID 178485735, compound

HRID 491789Notes

Reaction equation

HRID 491789 reaction equation
[CH:1]([N:3]([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)[CH3:4])=[O: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]([N:3]([CH:1]=[O:2])[CH3:4])[CH2:6][CH2:7]3)=[O:12])[C:18]=2[CH:19]=1)([OH:25])=[O:24]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178497419HCID 178497419, compound

Product 1

HCID 178485735HCID 178485735, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Trans-3-[4-(N-formyl-N-methylamino)cyclohexylcarbonylamino]-5-methoxycarbonyl-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide (1.90 g) obtained in Example 234 is suspended in tetrahydrofuran/methanol (1:1, 50 ml), and thereto is added 4N aqueous sodium hydroxide solution (5 ml) under ice-cooling. The mixture is warmed to room temperature, and stirred for 17 hours. The reaction solution is concentrated under reduced pressure, and to the residue is poured ice-water, and the mixture is neutralized with 10% hydrochloric acid. The precipitates are collected by filtration, washed successively with water and tetrahydrofuran, and dried to give the title compound (1.59 g).

Workup

  1. temperaturecooling
  2. concentrationThe reaction solution is concentrated under reduced pressure
  3. additionto the residue is poured ice-water
  4. filtrationThe precipitates are collected by filtration
  5. washwashed successively with water and tetrahydrofuran
  6. customdried

Sources & evidence

ORD record
ord-f348ab4997c243e5aa195c0fb8180061
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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