Trifluoroacetic acid → 3-(1-Cyclopropyl-5-fluoro-2,3-dihydro-1H-inden-1-yl)-7-[(methylsulfanyl)methyl]-1H-indole

HRID 561576ノート

反応式

HRID 561576 の反応式
[CH:1]1([C:4]2(O)[C:12]3[C:7](=[CH:8][C:9]([F:13])=[CH:10][CH:11]=3)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1.[CH3:15][S:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]2[C:26]=1[NH:25][CH:24]=[CH:23]2.FC(F)(F)C(O)=O.[Cl-].[NH4+]>ClCCl>[CH:1]1([C:4]2([C:23]3[C:22]4[C:26](=[C:18]([CH2:17][S:16][CH3:15])[CH:19]=[CH:20][CH:21]=4)[NH:25][CH:24]=3)[C:12]3[C:7](=[CH:8][C:9]([F:13])=[CH:10][CH:11]=3)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1

参加物

6

反応物 4

HCID 6422Trifluoroacetic acidHCID 25517Ammonium ChlorideHCID 532567411-Cyclopropyl-5-fluoroindan-1-olHCID 583921877-[(Methylsulfanyl)methyl]-1H-indole

生成物 1

HCID 583923643-(1-Cyclopropyl-5-fluoro-2,3-dihydro-1H-inden-1-yl)-7-[(methylsulfanyl)methyl]-1H-indole

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

200 mg (0.78 mmol) of the compound from Example 76A with a purity of 75% and 152 mg (0.86 mmol) of the compound from Example 8A were introduced into 3.8 ml of dichloromethane at 0° C., 0.07 ml (0.94 mmol) of trifluoroacetic acid was added, and the mixture was stirred at 0° C. for 4 h. It was diluted with dichloromethane and added to saturated aqueous ammonium chloride solution, the phases were separated, the aqueous phase was extracted with dichloromethane, and the combined organic phases were dried over magnesium sulfate, filtered and concentrated. The residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 175 mg (64% of theory) of the title compound.

後処理

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted with dichloromethane
  3. dry with materialthe combined organic phases were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)

出典と根拠

ORDレコード
ord-e386a73f1f9d40dcb05ae4cc9b4b5d17
出典データセット
uspto-grants-2011_11
特許番号
US08063234B2

反応ノート

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