Hydrochloride methanol → Morpholine-4-carboxylic acid [4-methoxy-7-(1,2,3,6-tetrahydro-pyridin-4-yl)-benzothiazol-2-yl]-amide hydrochloride

HRID 1582120Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[C:22]3[S:21][C:20]([NH:23][C:24]([N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)=[O:25])=[N:19][C:18]=3[C:17]([O:32][CH3:33])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:34].CO>>[ClH:34].[CH3:33][O:32][C:17]1[C:18]2[N:19]=[C:20]([NH:23][C:24]([N:26]3[CH2:27][CH2:28][O:29][CH2:30][CH2:31]3)=[O:25])[S:21][C:22]=2[C:14]([C:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=2)=[CH:15][CH:16]=1

Participants

Reactant 2

HCID 21893726Hydrochloride methanol

HCID 865888334-{4-methoxy-2-[(morpholine-4-carbonyl)-amino]-benzothiazol-7-yl}-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86588834Morpholine-4-carboxylic acid [4-methoxy-7-(1,2,3,6-tetrahydro-pyridin-4-yl)-benzothiazol-2-yl]-amide hydrochlorideYield 84%

Procedure

0.130 g (0.27 mMol) 4-{4-methoxy-2-[(morpholine-4-carbonyl)-amino]-benzothiazol-7-yl}-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester were dissolved in 3 ml 2.5 M HCl/MeOH and heated to reflux for 1.5 h. The reaction mixture was concentrated in vacuo and taken up in 3 ml isopropanol. The suspension formed was filtered and the material on the filter was washed with diethyl ether and dried in vacuo. One obtained 95 mg (84%) morpholine-4-carboxylic acid [4-methoxy-7-(1,2,3,6-tetrahydro-pyridin-4-yl)-benzothiazol-2-yl]-amide hydrochloride (1:1) as an off-white solid. ES-MS m/e (%): 375 ([M+H]+, 100).

Workup

temperatureheated
temperatureto reflux for 1.5 h
concentrationThe reaction mixture was concentrated in vacuo
customThe suspension formed
filtrationwas filtered
washthe material on the filter was washed with diethyl ether
customdried in vacuo

Sources & evidence

ORD record: ord-7bf8672132ef48009a52ca1c7e8fb555
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06734179B2

Reaction notes

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