Sodium Hydroxide → HCID 71063037, compound

HRID 875495Notes

Reaction equation

HRID 875495 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([Cl:35])[C:17]=1[C:18]([N:20]1[C:28]2[CH:27]=[CH:26][N:25]=[C:24]([NH:29][C:30]([CH:32]3[CH2:34][CH2:33]3)=[O:31])[C:23]=2[CH:22]=[CH:21]1)=[O:19])[C:5]([NH:7][C@H:8]([C:10]([O:12]CC)=[O:11])[CH3:9])=[O:6].[OH-].[Na+]>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([Cl:35])[C:17]=1[C:18]([N:20]1[C:28]2[CH:27]=[CH:26][N:25]=[C:24]([NH:29][C:30]([CH:32]3[CH2:34][CH2:33]3)=[O:31])[C:23]=2[CH:22]=[CH:21]1)=[O:19])[C:5]([NH:7][C@H:8]([C:10]([OH:12])=[O:11])[CH3:9])=[O:6]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 71618041HCID 71618041, compound

Product 1

HCID 71063037HCID 71063037, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl N-[3,5-dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)benzoyl]alaninate (20 mg, 0.038 mmol) in tetrahydrofuran and water (1:1, 1 mL) was treated with sodium hydroxide (1.5 mg) and stirred at room temperature for about 1 hour. Tetrahydrofuran was removed under vaccuo and the residue was acidified with hydrochloric acid solution (1N, upto pH 2). The solid was filtered and dried to get pure N-[3,5-dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)benzoyl]alanine (12 mg, 66%).

Workup

  1. customTetrahydrofuran was removed under vaccuo
  2. filtrationThe solid was filtered
  3. customdried

Sources & evidence

ORD record
ord-a70defb4e6bd4a5c8510dcaaf6baa1e7
Source dataset
uspto-grants-2015_03
Patent number
US08980911B2

Reaction notes

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