Triethylamine → 4-Fluorobenzenesulfonic 2-[(piperidine-4-carbonyl)amino]-benzothiazol-6-yl ester

HRID 1867954Notes

Reaction equation

HRID 1867954 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:26])[NH:15][C:16]2[S:17][C:18]3[CH:24]=[C:23]([OH:25])[CH:22]=[CH:21][C:19]=3[N:20]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[F:27][C:28]1[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1.C(N(CC)CC)C>CC(C)=O>[NH:8]1[CH2:9][CH2:10][CH:11]([C:14]([NH:15][C:16]2[S:17][C:18]3[CH:24]=[C:23]([O:25][S:34]([C:31]4[CH:32]=[CH:33][C:28]([F:27])=[CH:29][CH:30]=4)(=[O:36])=[O:35])[CH:22]=[CH:21][C:19]=3[N:20]=2)=[O:26])[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 579808374-(6-Hydroxybenzothiazol-2-ylcarbamoyl)piperidine-1-carboxylic acid tert-butyl ester2×

Product 1

HCID 579808454-Fluorobenzenesulfonic 2-[(piperidine-4-carbonyl)amino]-benzothiazol-6-yl esterYield 76.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 4-(6-hydroxybenzothiazol-2-ylcarbamoyl)piperidine-1-carboxylic acid tert-butyl ester (intermediate 2) (454 mg, 1.20 mmol), of 4-fluoro-benzenesulfonyl chloride (234 mg, 1.20 mmol) and of triethylamine (320 μl) in 10 ml of acetone is stirred at room temperature for 1 hour. The triethylamine hydrochloride is filtered off and the filtrate is evaporated. The crude reaction product is purified by column chromatography (eluent: EtOAc/heptane (7/3)) to give 400 mg of 4-fluorobenzenesulfonic 2-[(piperidine-4-carbonyl)amino]-benzothiazol-6-yl ester (white solid).

Workup

  1. filtrationThe triethylamine hydrochloride is filtered off
  2. customthe filtrate is evaporated
  3. customThe crude reaction product
  4. customis purified by column chromatography (eluent: EtOAc/heptane (7/3))

Sources & evidence

ORD record
ord-fdc4ed8c18db40f89ef5c5d42164be0b
Source dataset
uspto-grants-2009_12
Patent number
US07632952B2

Reaction notes

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