Pyridine → HCID 25000075、化合物

HRID 424144ノート

反応式

HRID 424144 の反応式
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]

参加物

6

反応物 3

HCID 1049PyridineHCID 124665981-Chloro-3-methylbutan-2-oneHCID 24829325HCID 24829325、化合物

生成物 1

HCID 25000075HCID 25000075、化合物収率 18%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-bfe4a251edd14d4c8d50929882aa8c41
出典データセット
uspto-grants-2012_01
特許番号
US08101773B2

反応ノート

読み込み中…