Water → HCID 118275229, 화합물

HRID 526009노트

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HRID 526009 반응식
[CH3:1][C:2]1[N:7]=[C:6]2[NH:8][C:9]([C:11](=[O:28])[NH:12][CH:13]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)[C:14]([F:17])([F:16])[F:15])=[CH:10][C:5]2=[CH:4][C:3]=1[C:29]([O:31][CH3:32])=[O:30].[H-].[Na+].I[CH2:36][CH3:37].O>CN(C)C=O.C(OCC)(=O)C>[CH2:36]([N:8]1[C:6]2=[N:7][C:2]([CH3:1])=[C:3]([C:29]([O:31][CH3:32])=[O:30])[CH:4]=[C:5]2[CH:10]=[C:9]1[C:11](=[O:28])[NH:12][CH:13]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=1)[C:14]([F:15])([F:16])[F:17])[CH3:37]

참가 물질

7

반응물 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 90039588HCID 90039588, 화합물

생성물 1

HCID 118275229HCID 118275229, 화합물수율 68.6%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

Methyl 6-methyl-2-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (1.58 g, 3.44 mmol) was dissolved under argon at 0° C. in N,N-dimethylformamide (35 ml). Sodium hydride (60%; 0.165 g, 4.12 mmol) was added and the mixture was stirred with ice cooling for 2 h. Iodoethane (0.643 g, 4.12 mmol) was added and the reaction mixture was thawed with stirring over 18 h. Water and ethyl acetate were added and the phases were separated. The organic phase was washed with saturated sodium chloride solution and dried over magnesium sulphate, and the solvent was removed under reduced pressure. The residue was chromatographed with cyclohexane/ethyl acetate (3/1) and gave 1.15 g (66% of theory) of methyl 1-ethyl-6-methyl-2-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate. HPLC-MS: log P=6.27; mass (m/z): 488.1 (M+H)+; 1HNMR (D6-DMSO): δ 1.20 (t, 3H), 2.83 (s, 3H), 3.87 (s, 3H), 4.59 (q, 2H), 6.30-6.34 (m, 1H), 7.42 (s, 1H), 7.70-7.84 (m, 2H), 8.06 (d, 1H), 7.93-7.97 (m, 1H), 8.21 (s, 1H), 8.67 (s, 1H).

후처리

  1. stirringwith stirring over 18 h
  2. customthe phases were separated
  3. washThe organic phase was washed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was chromatographed with cyclohexane/ethyl acetate (3/1)

출처 및 근거

ORD 기록
ord-c8a7ec36a09e4bb1ac12e657ac241002
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09345247B2

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