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Sodium Hydroxide → 1-{6-[4-(1H-Imidazol-1-yl)-5-oxo-2,5-dihydro-1H-pyrazol-1-yl]pyrimidin-4-yl}azetidine-3-carboxylic acid

HRID 2039487
Notes
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Reaction equation

HRID 2039487 reaction equation
Cl.[NH:2]1[CH2:5][CH:4]([C:6]([OH:8])=[O:7])[CH2:3]1.Cl.Cl[C:11]1[N:16]=[CH:15][N:14]=[C:13]([N:17]2[C:21](=[O:22])[C:20]([N:23]3[CH:27]=[CH:26][N:25]=[CH:24]3)=[CH:19][NH:18]2)[CH:12]=1.[OH-].[Na+]>O.C(O)C>[N:23]1([C:20]2[C:21](=[O:22])[N:17]([C:13]3[N:14]=[CH:15][N:16]=[C:11]([N:2]4[CH2:5][CH:4]([C:6]([OH:8])=[O:7])[CH2:3]4)[CH:12]=3)[NH:18][CH:19]=2)[CH:27]=[CH:26][N:25]=[CH:24]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 13374356Azetidine-3-carboxylic acid--hydrogen chloride (1/1)HCID 866352552-(6-Chloropyrimidin-4-yl)-4-(1H-imidazol-1-yl)-1,2-dihydro-3H-pyrazol-3-one hydrochloride

Product 1

HCID 579250711-{6-[4-(1H-Imidazol-1-yl)-5-oxo-2,5-dihydro-1H-pyrazol-1-yl]pyrimidin-4-yl}azetidine-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702
Ethanol
Solvent
HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

46 mg (0.3 mmol) of azetidine-3-carboxylic acid hydrochloride are initially charged in a mixture of 1 ml of water and 0.3 ml of ethanol. 100 mg (0.3 mmol) of the compound from Example 13A are added, and the mixture is stirred at 100° C. for 1 h. The reaction mixture is then adjusted to pH=7 using aqueous 1 N sodium hydroxide solution and stirred at 100° C. for 16 h. Once more, the mixture is adjusted to pH=7 using aqueous 1 N sodium hydroxide solution and reacted in a single mode microwave (Emrys Optimizer) at 150° C. for 1 h. The reaction mixture is concentrated under reduced pressure and purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient). Yield: 23 mg (21% of theory)

Workup

  1. stirringstirred at 100° C. for 16 h
  2. customreacted in a single mode microwave (Emrys Optimizer) at 150° C. for 1 h
  3. concentrationThe reaction mixture is concentrated under reduced pressure
  4. custompurified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-cb2f5d91b9d24496ab3eec34238b2c80
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08580778B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes