Hydrochloric Acid → 3-Nitro-5-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)pyridin-2-amine dihydrochloride

HRID 241224Notes

Reaction equation

CC([CH:5]1[CH2:11][N:10](C([O-])=O)[CH2:9][C:8]2[CH:15]=[C:16]([C:19]3[CH:20]=[N:21][C:22]([NH2:28])=[C:23]([N+:25]([O-:27])=[O:26])[CH:24]=3)[CH:17]=[CH:18][C:7]=2[O:6]1)(C)C.[ClH:29]>CO.O1CCOCC1>[ClH:29].[ClH:29].[N+:25]([C:23]1[C:22]([NH2:28])=[N:21][CH:20]=[C:19]([C:16]2[CH:17]=[CH:18][C:7]3[O:6][CH2:5][CH2:11][NH:10][CH2:9][C:8]=3[CH:15]=2)[CH:24]=1)([O-:27])=[O:26]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 1,1-dimethylethyl 7-(6-amino-5-nitropyridin-3-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (3.5 g, 9.1 mmol, example 26, step 1) in methanol (75 mL) and 4N hydrogen chloride in dioxane (11 mL) was stirred at 50° C. for 1.5 h and then concentrated. The resulting residue was triturated with a 10% methanol in diethyl ether solution (50 mL) to provide 3-nitro-5-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)pyridin-2-amine dihydrochloride (3.1 g, 95%) as a red solid. 1H NMR (400 MHz, d6-DMSO) δ 9.76 (bs, 2H), 8.80 (d, 1H), 8.60 (s, 1H), 7.90 (s, 1H), 7.73 (dd, 1H), 7.16 (d, 1H), 4.39 (bs, 2H), 4.25 (bs, 2H), 3.48 (bs, 2H); MS (EI) for C14H14N4O3: 287 (MH+).

Workup

concentrationconcentrated
customThe resulting residue was triturated with a 10% methanol in diethyl ether solution (50 mL)

Sources & evidence

ORD record: ord-c07bd3a62f7e49c6a32dbf3c639ef16d
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08648066B2

Reaction notes

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