Acetic Anhydride → HCID 77933908, compound

HRID 1878584Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][CH:31]=1)[CH:5]=[N:6][NH:7][C:8]1[CH:13]=[C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[N:11]2[N:20]=[C:21]([CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[CH:22]=[C:10]2[N:9]=1.[C:32](OC(=O)C)(=[O:34])[CH3:33]>C(Cl)Cl>[C:32]([N:26]1[CH2:25][CH2:24][CH:23]([C:21]2[CH:22]=[C:10]3[N:9]=[C:8]([NH:7][N:6]=[CH:5][C:4]4[CH:29]=[CH:30][CH:31]=[C:2]([CH3:1])[CH:3]=4)[CH:13]=[C:12]([N:14]4[CH2:19][CH2:18][O:17][CH2:16][CH2:15]4)[N:11]3[N:20]=2)[CH2:28][CH2:27]1)(=[O:34])[CH3:33]

Participants

Conditions

Temperature: 90 °C

Procedure

There was suspended, in methylene chloride (2 mL), N-(3-methyl-benzylidene)-N′-(7-morpholin-4-yl-2-piperidin-4-yl-pyrazolo[1,5-a]pyrimidin-5-yl)-hydrazine (31.0 mg, 0.0739 mM) and then acetic acid anhydride (1 mL) was added to the suspension. After this reaction liquid was heated to 90° C. and stirred for 15 minutes, the solvent was distilled off, the resulting residue was diluted with a saturated aqueous solution of sodium bicarbonate and then the mixture was extracted with ethyl acetate. The resulting extracts were combined, dried over anhydrous sodium sulfate, the solvent was distilled off and the resulting solid was washed with diethyl ether to thus give the title compound (25.0 mg, yield: 73%).

Workup

customAfter this reaction liquid
distillationthe solvent was distilled off
additionthe resulting residue was diluted with a saturated aqueous solution of sodium bicarbonate
extractionthe mixture was extracted with ethyl acetate
dry with materialdried over anhydrous sodium sulfate
distillationthe solvent was distilled off
washthe resulting solid was washed with diethyl ether

Sources & evidence

ORD record: ord-7c483d33413a4120a2ebe2098cd38903
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314098B2

Reaction notes

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