4-Chloro-7-methoxy-6-(2-methoxyethoxy)-2-(3-nitrophenyl)quinazoline → HCID 59361995, compound

HRID 1808528Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:17][CH3:18])=[C:9]([O:12][CH2:13][CH2:14][O:15][CH3:16])[CH:10]=2)[N:5]=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=2)[N:3]=1.[NH2:28][C:29]1[CH:30]=[C:31]2[C:35](=[CH:36][CH:37]=1)[N:34]([C:38]([O-:40])=[O:39])[N:33]=[CH:32]2>C(O)(C)C>[CH3:18][O:17][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:28][C:29]3[CH:30]=[C:31]4[C:35](=[CH:36][CH:37]=3)[N:34]([C:38]([O:40][C:11]([CH3:6])([CH3:2])[CH3:10])=[O:39])[N:33]=[CH:32]4)=[N:3][C:4]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=3)=[N:5]2)=[CH:10][C:9]=1[O:12][CH2:13][CH2:14][O:15][CH3:16]

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of 4-chloro-7-methoxy-6-(2-methoxyethoxy)-2-(3-nitrophenyl)quinazoline (0.500 g, 1.28 mmol) and 5-amino-1H-indazole-1-carboxylate (0.314 g, 1.34 mmol) in iso-propanol (30 mL) was heated at 95° C. for 30 minutes and at 95° C. for 8 h. The mixture was allowed to cool to RT and the solid was collected via filtration. The cake was washed with iso-propanol and Et2O, triturated with CH2Cl2 and EtOAc and dried in vacuo to give tert-Butyl 5-(7-methoxy-6-(2-methoxyethoxy)-2-(3-nitrophenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate (0.560 g, 0.955 mmol, 71%). MS 587 (M+1). HPLC retention time 7.21 mins.

Workup

temperatureto cool to RT
filtrationthe solid was collected via filtration
washThe cake was washed with iso-propanol and Et2O
customtriturated with CH2Cl2 and EtOAc
customdried in vacuo

Sources & evidence

ORD record: ord-47dbba3933a94c33ba210c77b365c463
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357693B2

Reaction notes

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