Pyridine → HCID 86672019, compound

HRID 473844Notes

Reaction equation

[C:1]([Cl:4])(Cl)=[O:2].N1C=CC=CC=1.C[C:12]1[N:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:15]2[CH:24]=[C:25]([C:28]3[CH:29]=[CH:30][C:31]4[O:37][CH2:36][CH2:35][NH:34][CH2:33][C:32]=4[CH:38]=3)[CH:26]=[CH:27][C:14]=2[N:13]=1>C(Cl)(Cl)Cl>[Cl:4][C:1]([N:34]1[CH2:33][C:32]2[CH:38]=[C:28]([C:25]3[CH:26]=[CH:27][C:14]4[N:13]=[CH:12][N:16]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[C:15]=4[CH:24]=3)[CH:29]=[CH:30][C:31]=2[O:37][CH2:36][CH2:35]1)=[O:2]

Participants

Conditions

Temperature: 0 °C

Procedure

Phosgene (20 W % in toluene) (190 uL, 0.38 mmol) was added by syringe to a 0° C. cooled solution of pyridine (100 uL, 1.2 mmol) in chloroform (3 mL) followed by addition of 1,1-dimethylethyl 2-methyl-6-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1H-benzimidazole-1-carboxylate as obtained in step 7 as a solution in chloroform (1 mL). The mixture was stirred for 15 minutes at 0° C. then partitioned with 10% aqueous citric acid. The organic phase was dried over anhydrous sodium sulfate then filtered and concentrated. The residue was purified by silica gel chromatography to give 1,1-dimethylethyl 6-[4-(chlorocarbonyl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]-1H-benzimidazole-1-carboxylate (62.6 mg, 59% yield) as a yellow amorphous residue. MS (EI) for C23H24ClN3O4: 442 (MH+).

Workup

customthen partitioned with 10% aqueous citric acid
dry with materialThe organic phase was dried over anhydrous sodium sulfate
filtrationthen filtered
concentrationconcentrated
customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-5cd700a42e3340268b9e9ba5fbab94b9
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637499B2

Reaction notes

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