Hydrogen chloride-ethyl acetate → 1-(2-chlorophenyl)-5-(9(4-chlorophenyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepin-2-yl)-1H-1,2,4-triazol-3-amine

HRID 886544Notes

Reaction equation

CCOC(C)=O.Cl.[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[C:19]([C:20]2[N:21]=[C:22]3[C:28]4[CH:29]=[CH:30][C:31]([C:33]5[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=5)=[CH:32][C:27]=4[O:26][CH2:25][CH2:24][N:23]3[CH:40]=2)=[N:18][C:17]([NH:41]C(=O)O)=[N:16]1>CCOC(C)=O>[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[C:19]([C:20]2[N:21]=[C:22]3[C:28]4[CH:29]=[CH:30][C:31]([C:33]5[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=5)=[CH:32][C:27]=4[O:26][CH2:25][CH2:24][N:23]3[CH:40]=2)=[N:18][C:17]([NH2:41])=[N:16]1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of EtOAc/HCl (20 mL) was added to 1-(2-chlorophenyl)-5-(9-(4-chlorophenyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepin-2-yl)-1H-1,2,4-triazol-3-ylcarbamic acid (270 mg, 0.6 mmol) in EtOAc (10 mL) in portions. The resulting mixture was stirred at 50° C. for 5 h. The reaction mixture was filtered and the solid was collected to give 570 (100 mg, 34%). 1H NMR (DMSO, 400 MHz) δ 7.73-7.69 (m, 5H), 7.63-7.61 (m, 2H), 7.55-7.52 (m, 1H), 7.48 (dd, J=2.0, 6.8 Hz, 2H), 7.28-7.25 (m, 2H), 4.80-4.30 (b, 2H), 4.45 (s, 4H). LCMS (ESI) m/z 489.1 (M+H+)

Workup

filtrationThe reaction mixture was filtered
customthe solid was collected

Sources & evidence

ORD record: ord-ba14abac2d3b42c2bc3cb0cc2ed8ec34
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242104B2

Reaction notes

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