Sodium Hydroxide → HCID 58180599, compound

HRID 1188043Notes

Reaction equation

HRID 1188043 reaction equation
[CH:1]1([N:4]([CH:33]2[CH2:35][CH2:34]2)[C:5]([C:7]2[N:30]([CH2:31][CH3:32])[C:10]3=[N:11][C:12]([NH:19][C:20]4[S:21][C:22]([C:25]([O:27]CC)=[O:26])=[CH:23][N:24]=4)=[C:13]4[N:17]=[CH:16][N:15]([CH3:18])[C:14]4=[C:9]3[CH:8]=2)=[O:6])[CH2:3][CH2:2]1.[OH-].[Na+]>CCO>[CH:33]1([N:4]([CH:1]2[CH2:2][CH2:3]2)[C:5]([C:7]2[N:30]([CH2:31][CH3:32])[C:10]3=[N:11][C:12]([NH:19][C:20]4[S:21][C:22]([C:25]([OH:27])=[O:26])=[CH:23][N:24]=4)=[C:13]4[N:17]=[CH:16][N:15]([CH3:18])[C:14]4=[C:9]3[CH:8]=2)=[O:6])[CH2:34][CH2:35]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58180547HCID 58180547, compound

Product 1

HCID 58180599HCID 58180599, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-(7-(dicyclopropylcarbamoyl)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-4-ylamino)thiazole-5-carboxylate (example 19, 14.6 mg, 0.030 mmol) in EtOH (296 μL) was added 1 N NaOH aqueous solution (296 μL). The reaction mixture was stirred at rt 3 h and stirred at 50° C. 18 h. After cooling to room temperature, ethanol was removed by concentration in vacuo. The residue was acidified with 1 N HCl and the solid product was collected by filtration. 2-(7-(Dicyclopropylcarbamoyl)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-4-ylamino)thiazole-5-carboxylic acid was isolated as a pale yellow solid which was used crude in the next reaction.

Workup

  1. stirringstirred at 50° C
  2. custom18 h
  3. temperatureAfter cooling to room temperature
  4. customethanol was removed by concentration in vacuo
  5. filtrationthe solid product was collected by filtration

Sources & evidence

ORD record
ord-c7ab08368ab5454f816b4b1928b76ca1
Source dataset
uspto-grants-2014_03
Patent number
US08673933B2

Reaction notes

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