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Hydrazine hydrate (1:1) → 2-amino-N-[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]acetamide

HRID 1247833
Notes
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Reaction equation

HRID 1247833 reaction equation
O.NN.O=C1C2C(=CC=CC=2)C(=O)[N:6]1[CH2:15][C:16]([NH:18][C:19]1[CH:20]=[N:21][N:22]([CH3:44])[C:23]=1[NH:24][C:25]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:17]>C(O)C.O1CCCC1>[NH2:6][CH2:15][C:16]([NH:18][C:19]1[CH:20]=[N:21][N:22]([CH3:44])[C:23]=1[NH:24][C:25]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:17]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 219045342-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N-[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]acetamide

Product 1

HCID 219045762-amino-N-[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]acetamideYield 81.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
70 °C

Procedure

Hydrazine monohydrate (1.46 ml) was added to a solution of 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N-[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]acetamide (5.42 g) in ethanol (108 ml) and tetrahydrofuran (54 ml) at room temperature, and the mixture was stirred at 70° C. for 2 hours. The reaction mixture was cooled to 0° C., and the insoluble materials were removed by filtration. The filtrate was concentrated in vacuo. The residue was triturated with diisopropyl ether, collected by filtration and dried in vacuo to give 2-amino-N-[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]acetamide (3.37 g) as a solid. This product was used in the next step without further purification.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customthe insoluble materials were removed by filtration
  3. concentrationThe filtrate was concentrated in vacuo
  4. customThe residue was triturated with diisopropyl ether
  5. filtrationcollected by filtration
  6. customdried in vacuo

Sources & evidence

ORD record
ord-8b6ef869bf6548c582f6ad9026a37f7d
Source dataset
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07129232B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes