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Hydrazine hydrate (1:1) → 2-(4-(7-Amino-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetohydrazide

HRID 2047078
Notes
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Reaction equation

HRID 2047078 reaction equation
C[Si](C)(C)CCOC[N:7](COCC[Si](C)(C)C)[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:21][CH:22]=3)=[C:12]2[N:11]=[C:10]([CH:29]2[CH2:34][CH2:33][CH:32]([CH2:35][C:36]([O:38]CC)=O)[CH2:31][CH2:30]2)[C:9]=1Br.O.[NH2:53][NH2:54]>CN(C=O)C>[NH2:7][C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)=[CH:21][CH:22]=3)=[C:12]2[N:11]=[C:10]([CH:29]2[CH2:30][CH2:31][CH:32]([CH2:35][C:36]([NH:53][NH2:54])=[O:38])[CH2:33][CH2:34]2)[CH:9]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66733557Ethyl 2-(4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-bromo-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetate

Product 1

HCID 469463452-(4-(7-Amino-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetohydrazide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a 2-5 mL pressure vial was charged ethyl 2-(4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-bromo-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetate (0.12 mmol, 95 mg), DMF (1 mL), and hydrazine monohydrate (1 mL). The pressure vial was sealed and heated to 80° C. for 18 hours. After 18 hours, the solvents were removed in vacuo and the product taken on without further purification.

Workup

  1. customThe pressure vial was sealed
  2. customthe solvents were removed in vacuo
  3. customthe product taken on without further purification

Sources & evidence

ORD record
ord-e69eb99a242f4940aeaa3f69178c8109
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08591943B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes