Sodium hydride → 1-methyl-5,10-dihydrobenzo[b]pyrazolo[3,4-e][1,4]diazepin-4(1H)-one

HRID 220795

Reaction equation

CS([CH2-])=O.[Na+].[H-].[Na+].C([O:10][C:11]([C:13]1[CH:14]=[N:15][N:16]([CH3:26])[C:17]=1[NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH2:25])=O)C>CS(C)=O>[CH3:26][N:16]1[C:17]2[NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[NH:25][C:11](=[O:10])[C:13]=2[CH:14]=[N:15]1

Participants

Conditions

Temperature: 65 °C

Procedure

Sodium (methylsulphinyl)methanide (29.7 mmol) was pre-pared from sodium hydride (60% dispersion in oil, 1.19 g, 29.7 mmol) and anhydrous dimethyl sulphoxide (7 ml) by heating at 65° C. until a solution was observed. To this was added a solution of 5-(2-amino-phenylamino)-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester from Example E11.2 (3.63 g, 16.9 mmol) in anhydrous dimethyl sulphoxide (10 ml), and stirring continued at 65° C. for 2.5 h. The mixture was poured into ice (100 ml), and the resulting solid collected and purified by recrystallisation from methanol/EtOAc/60-80 pet ether to yield the title compound (1.46 g, 40%).

Workup

customthe resulting solid collected
custompurified by recrystallisation from methanol/EtOAc/60-80 pet ether

Sources & evidence

ORD record: ord-3e583a73eb614ed2a392213d44410395
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202858B2

Linked notes

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