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Hydrochloric Acid → 2-((6-(4-(2-Hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-yl)amino)-1,3-thiazole-5-carboxylic acid

HRID 515249
Notes
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Reaction equation

HRID 515249 reaction equation
[OH-].[Li+].[OH:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[N:17]=[C:16]([CH3:18])[N:15]=[C:14]([NH:19][C:20]3[S:21][C:22]([C:25]([O:27]C)=[O:26])=[CH:23][N:24]=3)[CH:13]=2)[CH2:8][CH2:7]1.Cl>O>[OH:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[N:17]=[C:16]([CH3:18])[N:15]=[C:14]([NH:19][C:20]3[S:21][C:22]([C:25]([OH:27])=[O:26])=[CH:23][N:24]=3)[CH:13]=2)[CH2:8][CH2:7]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 49821888Methyl Hydroxyethyl Piperazinyl Methyl Pyrimidinylamino Thiazolecarboxylate2×

Product 1

HCID 498222172-((6-(4-(2-Hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-yl)amino)-1,3-thiazole-5-carboxylic acidYield 96.7%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

Lithium hydroxide (23.4 g, 0.35 mol) and water (265 mL) were mixed in four-necked flask and dissolved by stirring, and then methyl 2-(6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazole-5-formate (Compound 6) (37.8 g, 0.1 mol) was added. After reaction at 50° C. for 3 h, cooled down to room temperature and pH value was adjusted to 6-6.5 by hydrochloric acid (6N). In cold storage grew the grain overnight. After suction filtration, the cake was dried to constant weight to give target Compound 7 (35.2 g, yield: 96.7%).

Workup

  1. dissolutiondissolved
  2. customAfter reaction at 50° C. for 3 h
  3. customthe grain overnight
  4. filtrationAfter suction filtration
  5. customthe cake was dried to constant weight

Sources & evidence

ORD record
ord-a56d9d488d5f4216a227b6625b7a3a79
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09108954B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes