4-{[4-Chloro-3-(trifluoromethyl)benzyl]amino}-6-nitroquinazoline-8-carboxamide → 6-Amino-4-{[4-chloro-3-(trifluoromethyl)benzyl]amino}quinazoline-8-carboxamide

HRID 474409Notes

Reaction equation

[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]2[C:17]3[C:12](=[C:13]([C:21]([NH2:23])=[O:22])[CH:14]=[C:15]([N+:18]([O-])=O)[CH:16]=3)[N:11]=[CH:10][N:9]=2)=[CH:4][C:3]=1[C:26]([F:29])([F:28])[F:27]>C(O)(=O)C.[Zn]>[NH2:18][C:15]1[CH:16]=[C:17]2[C:12](=[C:13]([C:21]([NH2:23])=[O:22])[CH:14]=1)[N:11]=[CH:10][N:9]=[C:8]2[NH:7][CH2:6][C:5]1[CH:24]=[CH:25][C:2]([Cl:1])=[C:3]([C:26]([F:28])([F:29])[F:27])[CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Zinc powder (115 mg, 1.76 mmol, 5.0 equiv.) was added to a suspension of 4-{[4-chloro-3-(trifluoromethyl)benzyl]amino}-6-nitroquinazoline-8-carboxamide (150 mg, 0.35 mmol, 1.0 equiv.) in acetic acid (12 mL). The resulting mixture was stirred at 80° C. for 10 min. The reaction mixture was filtered. The filtrate was concentrated and purified by pre-HPLC to yield the title compound as yellow solid in 68% yield. Mass: M+H+: 396.

Workup

filtrationThe reaction mixture was filtered
concentrationThe filtrate was concentrated
custompurified by pre-HPLC

Sources & evidence

ORD record: ord-a82dd1adb73d46b1a89050aafaab93db
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637532B2

Reaction notes

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