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

HRID 1803269ノート

反応式

HRID 1803269 の反応式
Br[CH:2]1[CH2:7][CH2:6][CH2:5][C:4](=O)[C:3]1=[O:9].[CH3:10][O:11][C:12]1[CH:13]=[C:14]([NH:24][C:25]([NH2:27])=[S:26])[CH:15]=[CH:16][C:17]=1[N:18]1[CH:22]=[N:21][C:20]([CH3:23])=[N:19]1>C(O)C.CCOC(C)=O>[CH3:10][O:11][C:12]1[CH:13]=[C:14]([NH:24][C:25]2[S:26][C:7]3[CH2:6][CH2:5][CH2:4][C:3](=[O:9])[C:2]=3[N:27]=2)[CH:15]=[CH:16][C:17]=1[N:18]1[CH:22]=[N:21][C:20]([CH3:23])=[N:19]1

参加物

5

反応物 2

HCID 134385013-Bromocyclohexane-1,2-dioneHCID 866498981-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)thiourea

生成物 1

HCID 866499272-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylamino)-6,7-dihydrobenzo[d]thiazol-4(5H)-one収率 44%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 3-bromocyclohexane-1,2dione (158 mg, 0.827 mmol, from preparation AAE) and 1-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)thiourea (109 mg, 0.414 mmol, from step 4 of preparation F) was heated in ethanol (1.4 mL) at 80° C. for 12 h. The crude reaction was diluted with EtOAc and washed with saturated sodium bicarbonate solution. The organic layer was concentrated in vacuo. The crude product was purified using preparatory TLC (80% acetone/hexanes) to afford 2-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylamino)-6,7-dihydrobenzo[d]thiazol-4(5H)-one (64 mg, 44% yield) as a yellow solid. LC-MS (M+H)+ 356.3. 1H NMR (400 MHz, chloroform-d) δ ppm 8.55 (s, 1 H) 7.68 (d, J=8.56 Hz, 1 H) 7.31 (d, J=2.27 Hz, 1 H) 6.96 (dd, J=8.56, 2.52 Hz, 1 H) 3.95 (s, 3H) 3.00 (t, J=6.04 Hz, 2 H) 2.59-2.68 (m, 2 H) 2.45-2.52 (m, 3H) 2.20-2.31 (m, 2H).

後処理

  1. customThe crude reaction
  2. washwashed with saturated sodium bicarbonate solution
  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-6c147d0da6944f0491aa71fe5b00fe1a
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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