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 1803270ノート

反応式

HRID 1803270 の反応式
[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

参加物

4

反応物 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、化合物

生成物 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-ol収率 59.1%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1e79eb94685a40b6ac759108977c3707
出典データセット
uspto-grants-2013_01
特許番号
US08349880B2

反応ノート

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