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Lithium hydroxide, monohydrate → 4-(5-Chloro-imidazo[1,2-a]pyridin-8-ylamino)-benzoic acid

HRID 552396
Notes
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Reaction equation

HRID 552396 reaction equation
C[O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[C:12]3[N:13]([CH:18]=[CH:19][N:20]=3)[C:14]([Cl:17])=[CH:15][CH:16]=2)=[CH:6][CH:5]=1.ClC1N2C=CN=C2C(NC2C=CC(N3CCN(C(C)C)CC3)=CC=2)=CC=1.O.[OH-].[Li+]>O1CCOCC1.O>[Cl:17][C:14]1[N:13]2[CH:18]=[CH:19][N:20]=[C:12]2[C:11]([NH:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:21])=[O:2])=[CH:5][CH:6]=2)=[CH:16][CH:15]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 575807224-(5-Chloro-imidazo[1,2-a]pyridin-8-ylamino)-benzoic acid methyl esterHCID 57580808(5-Chloro-imidazo[1,2-a]pyridin-8-yl)-[4-(4-isopropyl-piperazin-1-yl)-phenyl]-amine

Product 1

HCID 575806714-(5-Chloro-imidazo[1,2-a]pyridin-8-ylamino)-benzoic acid

Reagents, catalysts & solvents 1

HCID 21886435
1,4-Dioxane--water (1/1)
Solvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-(5-chloro-imidazo[1,2-a]pyridin-8-ylamino)-benzoic acid methyl ester (450 mg, 1.495 mmol), prepared using methods similar to those described for compound 12, step 1, and lithium hydroxide hydrate (250.9 mg, 5.98 mmol) in solution in dioxane/water (2/1: 30 mL) is heated at 60° C. for 2 hours. The mixture is concentrated and then acidified to pH 1 with aqueous 2N HCl. The resulting precipitate is filtrated to yield the title compound, which is used as such for the next step.

Workup

  1. customprepared
  2. concentrationThe mixture is concentrated
  3. filtrationThe resulting precipitate is filtrated

Sources & evidence

ORD record
ord-7288dddfc6f74019b2aaa1b4dc75c6c7
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07951818B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes