Hydrochloric Acid → 2-(3,4-Dimethoxy-phenylamino)-10-iodo-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one

HRID 544991Notes

Reaction equation

CN([CH:4]=[C:5]1[CH2:11][C:10](=[O:12])[NH:9][C:8]2[CH:13]=[CH:14][C:15]([I:17])=[CH:16][C:7]=2[C:6]1=O)C.C([O-])([O-])=O.[K+].[K+].[CH3:25][O:26][C:27]1[CH:28]=[C:29]([NH:35][C:36]([NH2:38])=[NH:37])[CH:30]=[CH:31][C:32]=1[O:33][CH3:34].Cl>CCO.O>[CH3:25][O:26][C:27]1[CH:28]=[C:29]([NH:35][C:36]2[N:38]=[CH:4][C:5]3[CH2:11][C:10](=[O:12])[NH:9][C:8]4[CH:13]=[CH:14][C:15]([I:17])=[CH:16][C:7]=4[C:6]=3[N:37]=2)[CH:30]=[CH:31][C:32]=1[O:33][CH3:34]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-dimethylaminomethylene-7-iodo-3,4-dihydro-1H-benzo[b]azepine-2,5-dione (v-a) (1.64 g, 4.6 mmol) in 50 mL EtOH was added K2CO3 (1.82 g, 11.04 mmol) and 1-(3,4-dimethoxyphenyl)guanidine (1.31 g, 5.06 mmol), and the reaction was heated to 80° C. for 12 h. The reaction was then cooled to 22° C., diluted with H2O, and treated with 1 M HCl to pH 3. The resulting solid was filtered and washed with H2O, followed by EtOH and Et2O. The crude product was dried in vacuo to give I-26 (1.8 g, 81%): HRMS Calcd. for C20H17IN4O3: 489.0423, Found 489.0431.

Workup

temperatureThe reaction was then cooled to 22° C.
filtrationThe resulting solid was filtered
washwashed with H2O
dry with materialThe crude product was dried in vacuo
customto give I-26 (1.8 g, 81%)

Sources & evidence

ORD record: ord-cf2ff34500a74fa0800c5a95f27584e1
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935694B2

Reaction notes

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