Hydrochloric Acid → HCID 57899137, compound

HRID 1036346Notes

Reaction equation

HRID 1036346 reaction equation
C([O:3][C:4]([C:6]1[C:7]([N:15]2[CH2:20][CH2:19][C:18]([C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=3)([CH2:21][N:22]3[C:30](=[O:31])[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:23]3=[O:32])[CH2:17][CH2:16]2)=[C:8]2[CH:14]=[CH:13][NH:12][C:9]2=[N:10][CH:11]=1)=[O:5])C.Cl>[OH-].[Na+].O1CCOCC1>[Cl:39][C:36]1[CH:35]=[CH:34][C:33]([C:18]2([CH2:21][N:22]3[C:23](=[O:32])[C:24]4[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:30]3=[O:31])[CH2:17][CH2:16][N:15]([C:7]3[C:6]([C:4]([OH:5])=[O:3])=[CH:11][N:10]=[C:9]4[NH:12][CH:13]=[CH:14][C:8]=34)[CH2:20][CH2:19]2)=[CH:38][CH:37]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57899149HCID 57899149, compound

Product 1

HCID 57899137HCID 57899137, compoundYield 97.1%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

4-[4-(4-Chlorophenyl)-4-(1,3-dioxo-1,3-dihydroisoindol-2-ylmethyl)-piperidin-1-yl]-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid ethyl ester (49 mg, 0.09 mmol) was hydrolysed in a mixture of 2M NaOH (1 mL) and 1,4-dioxane (1 mL) at 80° C. overnight. The solution was acidified by dropwise addition of conc. HCl. Solvents were evaporated and the resulting solid was filtered and washed with water, then dried. A white solid (45 mg) was obtained which was used in the next step without further purification.

Workup

  1. customSolvents were evaporated
  2. filtrationthe resulting solid was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-97c05edf6c994bee877a68d072d865d0
Source dataset
uspto-grants-2013_10
Patent number
US08546407B2

Reaction notes

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