1,2-Dichloroethane → HCID 59318349, 화합물

HRID 423347

반응식

HRID 423347 반응식
[CH3:1][CH:2]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][C:6]=1[C:14]([F:17])([F:16])[F:15])[CH3:3].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.O[NH:33][C:34](=[NH:51])[C:35]1[CH:43]=[CH:42][CH:41]=[C:40]2[C:36]=1[CH:37]=[CH:38][N:39]2[CH2:44][CH2:45][C:46]([O:48][CH2:49][CH3:50])=[O:47]>CN(C)C=O>[CH3:3][CH:2]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]2[O:11][N:51]=[C:34]([C:35]3[CH:43]=[CH:42][CH:41]=[C:40]4[C:36]=3[CH:37]=[CH:38][N:39]4[CH2:44][CH2:45][C:46]([O:48][CH2:49][CH3:50])=[O:47])[N:33]=2)=[CH:7][C:6]=1[C:14]([F:17])([F:16])[F:15])[CH3:1]

참가 물질

6

반응물 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 225977674-Isopropoxy-3-(trifluoromethyl)benzoic acidHCID 178471833HCID 178471833, 화합물

생성물 1

HCID 59318349HCID 59318349, 화합물수율 31.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

4-[(1-Methylethyl)oxy]-3-(trifluoromethyl)benzoic acid (D71) (136 mg, 0.55 mmol), EDC (116 mg, 0.61 mmol) and HOBt (82 mg, 0.61 mmol) were stirred in N,N-dimethylformamide (5 mL) for 20 min. Ethyl 3-{-4-[(hydroxyamino)(imino)methyl]-1H-indol-1-yl}propanoate (D57) (150 mg, 0.55 mmol) was added and the reaction stirred at room temperature for 3 h and then 80° C. for 18 h. The reaction mixture was partitioned between ethyl acetate (25 mL) and water (25 mL). The organic layer was washed with aqueous sodium bicarbonate (25 mL) and water (25 mL) before it was dried (phase separator), filtered and concentrated in vacuo. The residue was triturated with ethanol to give the title compound (85 mg). δH (d6-DMSO, 400 MHz): 8.44 (1H, dd), 8.35 (1H, d), 7.95 (1H, d), 7.81 (1H, d), 7.62-7.58 (2H, m), 7.36 (1H,app. t), 7.07 (1H, d), 4.99 (1H, septet), 4.54 (2H, t), 4.02 (2H, q), 2.89 (2H, t), 1.36 (6H, d), 1.11 (3H, t). MS (ES+): C26H24F3N3O4 requires 487; found 488 (MH+).

후처리

  1. wait80° C. for 18 h
  2. customThe reaction mixture was partitioned between ethyl acetate (25 mL) and water (25 mL)
  3. washThe organic layer was washed with aqueous sodium bicarbonate (25 mL) and water (25 mL) before it
  4. customwas dried (phase separator)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with ethanol

출처 및 근거

ORD 기록
ord-62b7b3651d5742e4a3ea7bc0a39afcaf
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101775B2

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