Pyridine → HCID 25000075, 화합물

HRID 424144노트

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HRID 424144 반응식
C(C1C=C([CH2+]=NC2C=CC(OC3C=CN=C(C(NC)=O)C=3)=CC=2F)N(C2C=[CH:34][CH:33]=[C:32]([CH2:36][OH:37])C=2)N=1)(C)(C)C.[C:38]([C:42]1[CH:46]=[C:45]([NH:47][C:48]([NH:50][C:51]2[CH:67]=[CH:66][C:54]([O:55][C:56]3[CH:61]=[CH:60][N:59]=[C:58]([C:62]([NH:64][CH3:65])=[O:63])[CH:57]=3)=[CH:53][C:52]=2[F:68])=[O:49])[N:44]([C:69]2[CH:74]=[CH:73][CH:72]=[C:71]([CH2:75][OH:76])[CH:70]=2)[N:43]=1)([CH3:41])([CH3:40])[CH3:39].N1C=CC=C[CH:78]=1.CC(C)C(=O)CCl>ClCCl.CCOC(C)=O>[CH3:78][CH:33]([CH3:34])[CH2:32][C:36]([O:76][CH2:75][C:71]1[CH:72]=[CH:73][CH:74]=[C:69]([N:44]2[C:45]([NH:47][C:48](=[O:49])[NH:50][C:51]3[CH:67]=[CH:66][C:54]([O:55][C:56]4[CH:61]=[CH:60][N:59]=[C:58]([C:62](=[O:63])[NH:64][CH3:65])[CH:57]=4)=[CH:53][C:52]=3[F:68])=[CH:46][C:42]([C:38]([CH3:41])([CH3:39])[CH3:40])=[N:43]2)[CH:70]=1)=[O:37]

참가 물질

6

반응물 3

HCID 1049PyridineHCID 124665981-Chloro-3-methylbutan-2-oneHCID 24829325HCID 24829325, 화합물

생성물 1

HCID 25000075HCID 25000075, 화합물수율 18%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a 0° C. solution of example 1, (4-{4-[({3-tert-butyl-1-[3-(hydroxymethyl)phenyl]-1H-pyrazol-5-yl}carbamoyl)amino]-3-fluorophenoxy}-N-methylpyridine-2-carboxamide, (0.10 g, 0.19 mmol) in dichloromethane (1.0 mL)/pyridine (0.3 mL) was added dropwise 3-methylbutanonyl chloride (0.02 mL, 0.23 mmol). The reaction mixture was allowed to warm to room temperature and stir for 72 h. The reaction mixture was diluted with EtOAc and washed with sat. aqueous NaHCO3. The combined organic layer was washed with brine, dried and concentrated. The crude material was purified via column chromatography (CH2Cl2: MeOH, 100% CH2Cl2 to 98.5:1.5) to afford 0.02 g (18%) of the desired product as a white solid. MS m/z 617.3 (M+H)+; Retention time (LC-MS): 3.89 min.

후처리

  1. washwashed with sat. aqueous NaHCO3
  2. washThe combined organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe crude material was purified via column chromatography (CH2Cl2: MeOH, 100% CH2Cl2 to 98.5:1.5)

출처 및 근거

ORD 기록
ord-bfe4a251edd14d4c8d50929882aa8c41
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101773B2

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