Trityl chloride → 1-isopropyl-5-tritylamino-1H-pyrazole-4-carbonitrile

HRID 349543Notes

Reaction equation

[NH2:1][C:2]1[N:6]([CH:7]([CH3:9])[CH3:8])[N:5]=[CH:4][C:3]=1[C:10]#[N:11].[C:12]1([C:18](Cl)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>N1C=CC=CC=1>[CH:7]([N:6]1[C:2]([NH:1][C:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[C:3]([C:10]#[N:11])[CH:4]=[N:5]1)([CH3:9])[CH3:8]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 5-amino-1-isopropyl-1H-pyrazole-4-carbonitrile (10.4 g) in pyridine (200 ml) was added triphenylmethyl chloride (23.2 g) at room temperature. The mixture was stirred at 60° C. for 5 hours. The reaction mixture was evaporated under reduced pressure and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, filtered, and evaporated vacuo. The residue was triturated with diisopropyl ether to give 1-isopropyl-5-tritylamino-1H-pyrazole-4-carbonitrile (19.1 g).

Workup

customThe reaction mixture was evaporated under reduced pressure
extractionextracted with ethyl acetate
dry with materialThe extract was dried over anhydrous magnesium sulfate
filtrationfiltered
customevaporated vacuo
customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record: ord-04cd6a1b73e745148db90add40911e49
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07179801B2

Reaction notes

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