Water → 3-(1-cyanocyclopropyl)-N-[3-({2-[(cyclopropylcarbonyl)amino]-1,3-benzothiazol-6-yl}oxy)-4-methoxyphenyl]benzamide

HRID 2190406노트

반응식

HRID 2190406 반응식
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]3[CH:13]=[C:14]([NH:20][C:21](=[O:33])[C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([C:28]5([C:31]#[N:32])[CH2:30][CH2:29]5)[CH:23]=4)[CH:15]=[CH:16][C:17]=3[O:18][CH3:19])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH:34]1([C:37](Cl)=[O:38])[CH2:36][CH2:35]1.O>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:31]([C:28]1([C:24]2[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=2)[C:21]([NH:20][C:14]2[CH:15]=[CH:16][C:17]([O:18][CH3:19])=[C:12]([O:11][C:9]3[CH:8]=[CH:7][C:5]4[N:6]=[C:2]([NH:1][C:37]([CH:34]5[CH2:36][CH2:35]5)=[O:38])[S:3][C:4]=4[CH:10]=3)[CH:13]=2)=[O:33])[CH2:30][CH2:29]1)#[N:32]

참가 물질

6

반응물 3

HCID 962WaterHCID 77637Cyclopropanecarbonyl chlorideHCID 86655365N-{3-[(2-amino-1,3-benzothiazol-6-yl)oxy]-4-methoxyphenyl}-3-(1-cyanocyclopropyl)benzamide

생성물 1

HCID 866553663-(1-cyanocyclopropyl)-N-[3-({2-[(cyclopropylcarbonyl)amino]-1,3-benzothiazol-6-yl}oxy)-4-methoxyphenyl]benzamide수율 55.3%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매

실험 절차

A solution of N-{3-[(2-amino-1,3-benzothiazol-6-yl)oxy]-4-methoxyphenyl}-3-(1-cyanocyclopropyl)benzamide (91 mg, 0.20 mmol), cyclopropanecarbonyl chloride (105 mg, 1.00 mmol) and N,N-dimethylpyridine-4-amine (122 mg, 1.00 mmol) in pyridine (2 mL) was stirred at room temperature for 18 hr. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (eluent:hexane/ethyl acetate=1:1), and triturated with diethyl ether to give the title compound (58 mg, 55%) as a pale-yellow solid.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (eluent:hexane/ethyl acetate=1:1)
  5. customtriturated with diethyl ether

출처 및 근거

ORD 기록
ord-5ebddf4f7dd54310a7679c8a0b954bff
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324395B2

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