Hydrochloride methanol → HCID 67134165, compound

HRID 2420856Notes

Reaction equation

C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([N:23]3[CH2:27][CH2:26][CH2:25][CH:24]3[CH2:28][OH:29])(=[O:22])=[O:21])=[CH:16][CH:15]=2)[N:9]=1)(C)(C)C.[ClH:31].CO>>[ClH:31].[NH2:7][C:8]1[N:9]=[C:10]([C:14]2[CH:15]=[CH:16][C:17]([S:20]([N:23]3[CH2:27][CH2:26][CH2:25][C@@H:24]3[CH2:28][OH:29])(=[O:22])=[O:21])=[CH:18][CH:19]=2)[CH:11]=[CH:12][CH:13]=1

Participants

Reactant 2

HCID 21893726Hydrochloride methanol

HCID 67134124HCID 67134124, compound

Product 1

HCID 67134165HCID 67134165, compoundYield 86%

Procedure

A solution of {6-[4-(2-hydroxymethyl-pyrrolidine-1-sulfonyl)-phenyl]pyridin-2-yl}carbamic acid tert-butyl ester (15.0 g, 34.6 mmol) in HCl/MeOH (50 mL, 2M) was heated at reflux for 2 h. After cooling to room temperature, the reaction mixture was evaporated under vacuum and washed with EtOAc to give (R)-(1-(4-(6-aminopyridin-2-yl)phenylsulfonyl)pyrrolidin-2-yl) methanol hydrochloride (C-2; 11.0 g, 86%). 1H NMR (300 MHz, DMSO-d6) δ 8.18 (d, J=8.7 Hz, 2H), 7.93-7.99 (m, 3H), 7.31 (d, J=7.2 Hz, 1H), 7.03 (d, J=8.7 Hz, 1H), 3.53-3.57 (m, 2H), 3.29-35 (m, 2H), 3.05-3.13 (m, 1H), 1.77-1.78 (m, 2H), 1.40-1.45 (m, 2H). MS (ESI) m/z (M+H)+ 334.2.

Workup

temperatureat reflux for 2 h
customthe reaction mixture was evaporated under vacuum
washwashed with EtOAc

Sources & evidence

ORD record: ord-77b818b6cd98436bb41accc4fc2f52ee
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07956052B2

Reaction notes

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