Hydrazine hydrate (1:1) → 6-(3-(3-isopropoxyphenylamino)-6-methyl-1H-indazol-7-yl)-N-methylquinazolin-2-amine

HRID 2092295Notes

Reaction equation

F[C:2]1[C:20]([C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[N:27]=[C:26]([NH:31][CH3:32])[N:25]=[CH:24]3)=[C:19]([CH3:33])[CH:18]=[CH:17][C:3]=1[C:4](=S)[NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH:13]([CH3:15])[CH3:14])[CH:7]=1.O.[NH2:35][NH2:36]>C(O)CCC>[CH:13]([O:12][C:8]1[CH:7]=[C:6]([NH:5][C:4]2[C:3]3[C:2](=[C:20]([C:21]4[CH:22]=[C:23]5[C:28](=[CH:29][CH:30]=4)[N:27]=[C:26]([NH:31][CH3:32])[N:25]=[CH:24]5)[C:19]([CH3:33])=[CH:18][CH:17]=3)[NH:36][N:35]=2)[CH:11]=[CH:10][CH:9]=1)([CH3:15])[CH3:14]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 2-fluoro-N-(3-isopropoxyphenyl)-4-methyl-3-(2-(methylamino)quinazolin-6-yl)benzothioamide (54 mg, 117 μmol) and hydrazine hydrate (11 μL, 234 μmol) in n-butanol (6 mL) was heated in a microwave reactor at 150° C. for 33 min. Solvent was removed and the residue was purified by preparative TLC (50% EtOAc/hexane) to give the title compound. MS (M+H)+ 439.

Workup

customSolvent was removed
customthe residue was purified by preparative TLC (50% EtOAc/hexane)

Sources & evidence

ORD record: ord-fc884b9f4cd84b5e81af428372815b77
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440674B2

Reaction notes

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