Hydrochloric Acid → (S)-1-(6-Fluoro-1-phenyl-1H-benzoimidazol-2-yl)ethylamine dihydrochloride

HRID 242870Notes

Reaction equation

C(OC(=O)[NH:7][C@H:8]([C:10](=O)[NH:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:9])(C)(C)C.[ClH:28]>O1CCOCC1>[ClH:28].[ClH:28].[F:18][C:15]1[CH:16]=[CH:17][C:12]2[N:11]=[C:10]([C@@H:8]([NH2:7])[CH3:9])[N:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:13]=2[CH:14]=1

Participants

Conditions

Temperature: 60 °C

Procedure

[(S)-1-(4-Fluoro-2-phenylaminophenylcarbamoyl)ethyl]carbamic acid tert-butyl ester (40 g, 0.11 mol) was dissolved in HCl in dioxane (4N, 135 mL) and the reaction mixture heated at 60° C. for 3 h. The reaction mixture was cooled to RT and seeded with a crystal of the desired product causing the product to crystallise. The product was collected by filtration and dried in vacuo to give the title compound as a purple solid (31.2 g, 89%). 1H NMR 400 MHz (DMSO-d6) δ: 8.94 (3H, br s), 7.81 (1H, dd, J=8.8, 4.9 Hz), 7.74-7.62 (5H, m), 7.25-7.18 (1H, m), 6.98 (1H, dd, J=9.0, 2.4), 4.41 (1H, quintet, J=6.3 Hz), 1.45 (3H, d, J=6.4 Hz). LCMS: RT=2.02 min, [M+H]+=256 (10%) [M−NH2]=239 (100%).

Workup

temperatureThe reaction mixture was cooled to RT

Sources & evidence

ORD record: ord-d2d0dc4b4dcd46bfbbd38f5fce4dce69
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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