Hydrochloride methanol → 4-fluoro-N-[4-methoxy-7-(1,2,3,6-tetrahydro-pyridin-4-yl)-benzothiazol-2-yl]-benzamide hydrochloride

HRID 1582116Notes

Reaction equation

HRID 1582116 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](=[O:32])[C:25]4[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=4)=[N:19][C:18]=3[C:17]([O:33][CH3:34])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:35].CO>>[ClH:35].[F:31][C:28]1[CH:27]=[CH:26][C:25]([C:24]([NH:23][C:20]2[S:21][C:22]3[C:14]([C:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=4)=[CH:15][CH:16]=[C:17]([O:33][CH3:34])[C:18]=3[N:19]=2)=[O:32])=[CH:30][CH:29]=1

Participants

3

Reactant 2

HCID 21893726Hydrochloride methanolHCID 865888324-[2-(4-fluoro-benzoylamino)-4-methoxy-benzothiazol-7-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 227195504-fluoro-N-[4-methoxy-7-(1,2,3,6-tetrahydro-pyridin-4-yl)-benzothiazol-2-yl]-benzamide hydrochlorideYield 92%

Procedure

0.20 g (0.52 mMol) 4-[2-(4-fluoro-benzoylamino)-4-methoxy-benzothiazol-7-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester were dissolved in 5 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 4 ml isopropanol. The suspension formed was filtered and the material on the filter was washed with diethyl ether and dried in vacuo. One obtained 200 mg (92%) 4-fluoro-N-[4-methoxy-7-(1,2,3,6-tetrahydro-pyridin-4-yl)-benzothiazol-2-yl]-benzamide hydrochloride (1:1) as an off-white solid. F.p.: 268-275° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1.5 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customThe suspension formed
  5. filtrationwas filtered
  6. washthe material on the filter was washed with diethyl ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-ad010f8e748b4f5f81fa732b11096276
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

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