Hydrochloride methanol → HCID 86714273, compound

HRID 332944Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([CH2:14][O:15][C:16]2[C:25]3[C:24]([NH2:26])=[N:23][S:22](=[O:28])(=[O:27])[NH:21][C:20]=3[CH:19]=[CH:18][CH:17]=2)[CH2:9]1)=O)(C)(C)C.[ClH:29].CO>>[ClH:29].[NH2:26][C:24]1[C:25]2[C:16]([O:15][CH2:14][C@H:10]3[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]3)=[CH:17][CH:18]=[CH:19][C:20]=2[NH:21][S:22](=[O:27])(=[O:28])[N:23]=1

Participants

Reactant 2

HCID 21893726Hydrochloride methanol

HCID 86714275(S)-tert-butyl 3-(((4-amino-2,2-dioxido-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)methyl)piperidine-1-carboxylate

Product 1

HCID 86714273HCID 86714273, compoundYield 63.2%

Procedure

A solution of (S)-tert-butyl-3-(((4-amino-2,2-dioxido-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)methyl)piperidine-1-carboxylate (Example 2b, 7.0 g, 17.1 mmol) in conc. HCl:MeOH (1:1, 170 mL) was stirred at room temperature for 4 hours. The precipitate was collected by vacuum filtration, and dried to provide the desired product (3.75 g, 63.2%) as a white solid. 1H NMR (DMSO-d6, 400 MHz): δ 1.29 (m, 1H), 1.65 (m, 1H), 1.82 (m, 2H), 2.37 (m, 1H), 2.75 (m, 2H), 3.20 (d, J=8.0 Hz, 1H), 3.27 (d, J=11.2 Hz, 1H), 4.10 (d, J=6.0 Hz, 3H), 6.27 (d, J=8.4 Hz, 1H), 6.75 (d, J=8.4 Hz, 1H), 7.45 (t, J=8.4 Hz, 1H), 7.68 (s, 1H), 8.35 (br s, 1H), 8.74 (m, 1H), 9.05 (m, 1H), 10.98 (s, 1H). MS 311 (MH+).

Workup

filtrationThe precipitate was collected by vacuum filtration
customdried

Sources & evidence

ORD record: ord-600cdd7e801f4954abd1491c01df33d1
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877922B2

Reaction notes

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