1,2-Dichloroethane → HCID 59318425、化合物

HRID 423355ノート

反応式

HRID 423355 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=O.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[Cl:27][C:28]1[C:36]2[C:31](=[CH:32][CH:33]=[C:34]([C:37]([NH:39]O)=[NH:38])[CH:35]=2)[N:30]([CH2:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH:29]=1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:5]2[O:7][N:38]=[C:37]([C:34]3[CH:35]=[C:36]4[C:31](=[CH:32][CH:33]=3)[N:30]([CH2:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH:29]=[C:28]4[Cl:27])[N:39]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]

参加物

6

反応物 4

HCID 111,2-DichloroethaneHCID 668363-Bromo-4-methoxybenzoic acidHCID 757711-HydroxybenzotriazoleHCID 178471837ethyl 3-[3-chloro-5-[(Z)-N'-hydroxycarbamimidoyl]indol-1-yl]propanoate

生成物 1

HCID 59318425HCID 59318425、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

The 3-bromo-4-(methyloxy)benzoic acid (commercial: ICN) (243 mg, 1.05 mmol) stirring in DMF (10 ml) was treated with EDC (219 mg, 0.1.14 mmol) followed by HOBt (156 mg, 0.1.14 mmol). The resultant solution was stirred for 10 minutes. Added ethyl 3-{3-chloro-5-[(hydroxyamino)(imino)methyl]-1H-indol-1-yl}propanoate (D96) (324 mg, 1.05 mmol) and stirred at RT for 45 minutes. The solution was heated at 80° C. for 4 hours then left standing overnight. The solution was heated at 80° C. for a further 4 hours to give one major product. Evaporated off the DMF, added EtOAc (50 ml) and washed with water (50 ml). The EtOAc was washed with sat. aqueous sodium hydrogen carbonate (50 ml) and water (50 ml) then dried over MgSO4. Evaporated off the solvent and crystallised from ethanol to yield the title compound as 280 mg of cream solid. δH (400 MHz, d6-DMSO) 1.10 (3H, t), 2.90 (2H, t), 3.99-4.05 (5H, m), 4.49 (2H, t), 7.38 (1H, d), 7.74 (1H, s), 7.80 (1H, d), 7.97 (1H, d), 8.21-8.23 (2H, m), 8.36 (1H, d). MS (ES) C22H1981Br35ClN3O4 requires 505; found 506 (MH+).

後処理

  1. waitthen left
  2. temperatureThe solution was heated at 80° C. for a further 4 hours
  3. customto give one major product
  4. customEvaporated off the DMF
  5. additionadded EtOAc (50 ml)
  6. washwashed with water (50 ml)
  7. washThe EtOAc was washed with sat. aqueous sodium hydrogen carbonate (50 ml) and water (50 ml)
  8. dry with materialthen dried over MgSO4
  9. customEvaporated off the solvent
  10. customcrystallised from ethanol

出典と根拠

ORDレコード
ord-cf322d11f21f4b97bf8c87d2e910d806
出典データセット
uspto-grants-2012_01
特許番号
US08101775B2

反応ノート

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