HCID 23132495, compound → N2-(6,7-dimethoxyquinazolin-4-yl)benzothiazole-2,6-diamine

HRID 2108899Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[NH:15][C:16]1[S:17][C:18]2[CH:24]=[C:23]([N+:25]([O-])=O)[CH:22]=[CH:21][C:19]=2[N:20]=1.[H][H]>CN(C)C=O.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[NH:15][C:16]1[S:17][C:18]2[CH:24]=[C:23]([NH2:25])[CH:22]=[CH:21][C:19]=2[N:20]=1

Participants

Conditions

Temperature: 80 °C

Procedure

The crude (6,7-dimethoxyquinazolin-4-yl)-(6-nitrobenzothiazol-2-yl)amine (383 mg, 1 mmol) was dissolved in dimethylformamide (100 mL). Palladium on charcoal (106 mg, 10% Pd, 0.1 mmol Pd) was added and the air was replaced with hydrogen (1 bar). The mixture was vigorously stirred for 5 h at 80° C. and then filtered through Celite. After removal of the solvent in vacuo and subsequent drying, pure N2-(6,7-dimethoxyquinazolin-4-yl)benzothiazole-2,6-diamine was obtained as a tawny powder (202 mg, 0.57 mmol, 57%). LC/ESI-MS: m/z=354 [M+H]+; m/z=352 [M−H]−; Rt=2.15 mm.

Workup

filtrationfiltered through Celite
customAfter removal of the solvent in vacuo and subsequent drying

Sources & evidence

ORD record: ord-bcf0d66bb9ac4090b419f9f88e36e690
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07514460B2

Reaction notes

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