Acetic Anhydride → N-[7-(1-acetyl-1,2,3,6-tetrahydro-pyridin-4-yl)-4-methoxy-benzothiazol-2-yl]-4-fluoro-benzamide

HRID 1582117노트

반응식

HRID 1582117 반응식
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]([C:19]4[CH2:20][CH2:21][NH:22][CH2:23][CH:24]=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.[C:36](OC(=O)C)(=[O:38])[CH3:37].C(=O)(O)[O-].[Na+]>C1COCC1.O>[C:36]([N:22]1[CH2:21][CH:20]=[C: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:38])[CH3:37]

참가 물질

7

반응물 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 227195504-fluoro-N-[4-methoxy-7-(1,2,3,6-tetrahydro-pyridin-4-yl)-benzothiazol-2-yl]-benzamide hydrochloride

생성물 1

HCID 10287935N-[7-(1-acetyl-1,2,3,6-tetrahydro-pyridin-4-yl)-4-methoxy-benzothiazol-2-yl]-4-fluoro-benzamide수율 73.9%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 0.12 g (0.28 mMol) 4-fluoro-N-[4-methoxy-7-(1,2,3,6-tetrahydro-pyridin-4-yl)-benzothiazol-2-yl]-benzamide hydrochloride in 3 ml THF were added 0.043 ml triethyl amine. At 0° C. 0.029 ml (0.31 mMol) acetic anhydride was added dropwise and stirred for 30 min. Then a mixture of 5 ml sat. aqueous sodium bicarbonate and 15 ml water were added. After extracting with four times 25 ml ethyl acetate the combined organic phases were dried over sodium sulfate and concentrated to dryness in vacuo to yield 0.088 g (73%) N-[7-(1-acetyl-1,2,3,6-tetrahydro-pyridin-4-yl)-4-methoxy-benzothiazol-2-yl]-4-fluoro-benzamide as an off-white solid; F.p.: 264-265° C.

후처리

  1. customAt 0° C
  2. additionwere added
  3. extractionAfter extracting with four times 25 ml ethyl acetate the combined organic phases
  4. dry with materialwere dried over sodium sulfate
  5. concentrationconcentrated to dryness in vacuo

출처 및 근거

ORD 기록
ord-acbe95501df54322b58776b49953de03
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06734179B2

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