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

HRID 1247833Notes

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]

Participants

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

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