Hydrochloric Acid → (S)-(3-Fluoropyridin-2-yl)(4-(trifluoromethyl)phenyl)methanamine Hydrochloride

HRID 1622553

反応式

HRID 1622553 の反応式
[F:1][C:2]1[C:3]([C@H:8]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)[NH:9][S@](C(C)(C)C)=O)=[N:4][CH:5]=[CH:6][CH:7]=1.CCO.[ClH:29].CCOC(C)=O>C(Cl)Cl.O1CCOCC1>[ClH:29].[F:1][C:2]1[C:3]([C@H:8]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:24])([F:25])[F:23])=[CH:18][CH:17]=2)[NH2:9])=[N:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 8857Ethyl AcetateHCID 71144543(S)-N-((S)-(3-fluoropyridin-2-yl)(4(trifluoro-methyl)phenyl)methyl)-2-methylpropane-2-sulfinamide

生成物 1

HCID 71144279(S)-(3-Fluoropyridin-2-yl)(4-(trifluoromethyl)phenyl)methanamine Hydrochloride

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
0 °C

実験手順

To a cooled (0° C.) stirring solution of (S)—N—((S)-(3-fluoropyridin-2-yl)(4-(trifluoromethyl)phenyl)methyl)-2-methylpropane-2-sulfinamide (108 g, 288.8 mmol) in DCM:EtOH (1:1,1080 mL), was added saturated HCl in 1,4-dioxane (216 mL). Stirring was continued for 2 h at 0° C. The progress of reaction was monitored by TLC (100% EtOAc). After completion of the reaction, the reaction mixture was concentrated and triturated with Et2O to give a white solid which was filtered and dried to give (S)-(3-fluoropyridin-2-yl)(4-(trifluoromethyl)phenyl) methanamine hydrochloride as a white solid. 1H-NMR (400 MHz, CDCl3) δ ppm 9.23 (s, 3H), 8.60 (d, J=4.8 Hz, 1H), 7.87 (d, J=1.2 Hz, 1H), 7.84 (d, J=8.4 Hz, 2H), 7.72 (d, J=8.4 Hz, 2H), 7.59-7.63 (m, 1H), 6.09 (s, 1H). MS (ESI pos. ion) m/z: 270.1 (M+H).

後処理

  1. customThe progress of reaction
  2. customAfter completion of the reaction
  3. concentrationthe reaction mixture was concentrated
  4. customtriturated with Et2O
  5. customto give a white solid which
  6. filtrationwas filtered
  7. customdried

出典と根拠

ORDレコード
ord-d1891e70780f414a93266903d31d5f53
出典データセット
uspto-grants-2014_07
特許番号
US08778941B2

関連ノート

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