2-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylamino)-6,7-dihydrobenzo[d]thiazol-4(5H)-one → 2-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylamino)-4-phenyl-4,5,6,7-tetrahydrobenzo[d]thiazol-4-ol

HRID 1803270노트

반응식

HRID 1803270 반응식
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([NH:23][C:24]2[S:25][C:26]3[CH2:32][CH2:31][CH2:30][C:29](=[O:33])[C:27]=3[N:28]=2)[CH:14]=[CH:15][C:16]=1[N:17]1[CH:21]=[N:20][C:19]([CH3:22])=[N:18]1>C(OCC)C>[CH3:9][O:10][C:11]1[CH:12]=[C:13]([NH:23][C:24]2[S:25][C:26]3[CH2:32][CH2:31][CH2:30][C:29]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)([OH:33])[C:27]=3[N:28]=2)[CH:14]=[CH:15][C:16]=1[N:17]1[CH:21]=[N:20][C:19]([CH3:22])=[N:18]1

참가 물질

4

반응물 2

HCID 866499272-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylamino)-6,7-dihydrobenzo[d]thiazol-4(5H)-oneHCID 178418255HCID 178418255, 화합물

생성물 1

HCID 581100282-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylamino)-4-phenyl-4,5,6,7-tetrahydrobenzo[d]thiazol-4-ol수율 59.1%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

Phenylmagnesium bromide (1.0 M in THF, 0.118 mL, 0.118 mmol) was added to a rt solution of 2-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylamino)-6,7-dihydrobenzo[d]thiazol-4(5H)-one (14 mg, 0.039 mmol) in diethyl ether (0.13 mL). The reaction was quenched with saturated ammonium chloride and extracted with EtOAc. The organic layer was concentrated in vacuo. The crude product was purified using preparatory TLC (60% acetone/hexanes) to afford 10 mg (53% yield) of the titled compound as a oil. LC-MS (M+H)+ 434.3.

후처리

  1. customThe reaction was quenched with saturated ammonium chloride
  2. extractionextracted with EtOAc
  3. concentrationThe organic layer was concentrated in vacuo
  4. customThe crude product was purified

출처 및 근거

ORD 기록
ord-1e79eb94685a40b6ac759108977c3707
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08349880B2

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