Dimethylformamide → HCID 71053054, 화합물

HRID 869990노트

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HRID 869990 반응식
[F:1][C:2]1([F:31])[O:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]3([C:14]([NH:16][C:17]4[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([C:24]5[CH:29]=[CH:28][C:27](=[O:30])[NH:26][CH:25]=5)[N:18]=4)=[O:15])[CH2:13][CH2:12]3)=[CH:10][C:4]=2[O:3]1.Cl[CH2:33][C@@H:34]1[CH2:38][O:37]C(C)(C)[O:35]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>ClCCl>[F:31][C:2]1([F:1])[O:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]3([C:14]([NH:16][C:17]4[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([C:24]5[CH:29]=[CH:28][C:27](=[O:30])[N:26]([CH2:33][C@@H:34]([OH:35])[CH2:38][OH:37])[CH:25]=5)[N:18]=4)=[O:15])[CH2:13][CH2:12]3)=[CH:10][C:4]=2[O:3]1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 6930483(S)-4-Chloromethyl-2,2-dimethyl-1,3-dioxolaneHCID 251183661-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)-n-(5-methyl-6-(6-oxo-1,6-dihydropyridin-3-yl)pyridin-2-yl)cyclopropanecarboxamide

생성물 1

HCID 71053054HCID 71053054, 화합물수율 27%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
100 °C

실험 절차

To 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-N-(5-methyl-6-(6-oxo-1,6-dihydropyridin-3-yl)pyridin-2-yl)cyclopropanecarboxamide (0.15 g, 0.35 mmol), (S)-4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane (0.27 g, 1.8 mmol), and potassium carbonate (0.5 g, 3.5 mmol) was added N,N-dimethylformamide and the reaction mixture was heated to 100° C. overnight. The reaction was diluted with dichloromethane (20 mL) and washed with 1N hydrochloric acid (10 mL) and a saturated aqueous sodium bicarbonate solution (10 mL). The organics were dried over sodium sulfate and evaporated. The crude residue was purified by silica gel chromatography (eluting with 0-10% methanol in dichloromethane) to yield the product (47 mg, 27%). ESI-MS m/z calc. 499.16. found 500.2 (M+1)+. Retention time 1.53 minutes.

후처리

  1. washwashed with 1N hydrochloric acid (10 mL)
  2. dry with materialThe organics were dried over sodium sulfate
  3. customevaporated
  4. customThe crude residue was purified by silica gel chromatography (eluting with 0-10% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-ec7a55a7274c4c89ae0ff4c0b332149a
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969386B2

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