Water → 4-oxo-N-(6-(pyrrolidin-1-ylmethyl)pyridin-2-yl)-2-(3-(trifluoromethyl)phenyl)-4H-chromene-8-carboxamide

HRID 876540ノート

反応式

HRID 876540 の反応式
CCN(C(C)C)C(C)C.[O:10]=[C:11]1[C:20]2[C:15](=[C:16]([C:21](Cl)=[O:22])[CH:17]=[CH:18][CH:19]=2)[O:14][C:13]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=2)=[CH:12]1.Cl.[N:35]1([CH2:40][C:41]2[N:46]=[C:45]([NH2:47])[CH:44]=[CH:43][CH:42]=2)[CH2:39][CH2:38][CH2:37][CH2:36]1.O>CC#N>[O:10]=[C:11]1[C:20]2[C:15](=[C:16]([C:21]([NH:47][C:45]3[CH:44]=[CH:43][CH:42]=[C:41]([CH2:40][N:35]4[CH2:39][CH2:38][CH2:37][CH2:36]4)[N:46]=3)=[O:22])[CH:17]=[CH:18][CH:19]=2)[O:14][C:13]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=2)=[CH:12]1

参加物

6

反応物 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 584773264-oxo-2-(3-(trifluoromethyl)phenyl)-4H-chromene-8-carbonyl chlorideHCID 672957736-(Pyrrolidin-1-ylmethyl)pyridin-2-amine hydrochloride

生成物 1

HCID 584772604-oxo-N-(6-(pyrrolidin-1-ylmethyl)pyridin-2-yl)-2-(3-(trifluoromethyl)phenyl)-4H-chromene-8-carboxamide収率 40%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
60 °C

実験手順

DIPEA (125 mL, 0.705 mmol) was added to a solution of 4-oxo-2-(3-(trifluoromethyl)phenyl)-4H-chromene-8-carbonyl chloride 37 (83 mg, 0.235 mmol) and 6-(pyrrolidin-1-ylmethyl)pyridin-2-amine hydrochloride 49 (75 mg, 0.353 mmol) in CH3CN (15 mL). The reaction mixture was heated at 60° C. for 12 h, cooled to room temperature and poured into H2O. The mixture was extracted with CH2Cl2. The combined organics were dried (MgSO4) and concentrated. The crude residue was purified by MPLC eluting with CH2Cl2/MeOH (0-10%) to give Compound 243 (46 mg, 40% yield). MS (ESI) calcd for C27H22F3N3O3: 493.16. found: 494 [M+H].

後処理

  1. temperaturecooled to room temperature
  2. extractionThe mixture was extracted with CH2Cl2
  3. dry with materialThe combined organics were dried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude residue was purified by MPLC
  6. washeluting with CH2Cl2/MeOH (0-10%)

出典と根拠

ORDレコード
ord-14e86065c53b41069cb0314a66020b16
出典データセット
uspto-grants-2015_03
特許番号
US08987258B2

反応ノート

読み込み中…