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Methyl chloroformate → 4-[2-(4-Fluoro-benzoylamino)-4-methoxy-benzothiazol-7-yl]-piperidine-1-carboxylic acid methyl ester

HRID 1582152
Notes
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Reaction equation

HRID 1582152 reaction equation
Cl.[F:2][C:3]1[CH:28]=[CH:27][C:6]([C:7]([NH:9][C:10]2[S:11][C:12]3[C:18]([CH:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)=[CH:17][CH:16]=[C:15]([O:25][CH3:26])[C:13]=3[N:14]=2)=[O:8])=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:36][O:37][C:38](Cl)=[O:39].C(=O)(O)[O-].[Na+]>C1COCC1.O>[CH3:36][O:37][C:38]([N:22]1[CH2:21][CH2:20][CH:19]([C:18]2[C:12]3[S:11][C:10]([NH:9][C:7](=[O:8])[C:6]4[CH:5]=[CH:4][C:3]([F:2])=[CH:28][CH:27]=4)=[N:14][C:13]=3[C:15]([O:25][CH3:26])=[CH:16][CH:17]=2)[CH2:24][CH2:23]1)=[O:39]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 227195404-fluoro-N-[4-methoxy-7-piperidine-4-yl-benzothiazol-2-yl]-benzamide hydrochloride

Product 1

HCID 865888494-[2-(4-Fluoro-benzoylamino)-4-methoxy-benzothiazol-7-yl]-piperidine-1-carboxylic acid methyl esterYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 0.1 g (0.24 mMol) 4-fluoro-N-[4-methoxy-7-piperidine-4-yl-benzothiazol-2-yl]-benzamide hydrochloride (1:1) in 3 ml THF were added 0.036 ml triethyl amine. At 0° C. 0.020 ml (0.26 mMol) chloro formic acid methyl ester was added dropwise and stirred for 1 h. Then a mixture of 5 ml sat. aqueous sodium bicarbonate and 10 ml water were added. This was extracted three times with 15 ml ethyl acetate, the combined organic phase were dried over sodium sulfate and evaporated to dryness in vacuo. One obtained 0.080 g (76%) 4-[2-(4-fluoro-benzoylamino)-4-methoxy-benzothiazol-7-yl]-piperidine-1-carboxylic acid methyl ester as a white solid. F.p.: 238-239° C.

Workup

  1. customAt 0° C
  2. additionwere added
  3. extractionThis was extracted three times with 15 ml ethyl acetate
  4. dry with materialthe combined organic phase were dried over sodium sulfate
  5. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-5e8e962b81264ab383f45e3478f5810d
Source dataset
uspto-grants-2004_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06734179B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes