1,1,1-Trifluoro-3-iodopropane → N-{[(2S)-7-(Methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methyl}-N-(3,3,3-trifluoropropyl)amine

HRID 38924

반응식

HRID 38924 반응식
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH2:12][C@H:11]([CH2:14][NH2:15])[O:10][C:9]=2[CH:16]=1)(=[O:4])=[O:3].[F:17][C:18]([F:23])([F:22])[CH2:19][CH2:20]I>C(#N)C>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH2:12][C@H:11]([CH2:14][NH:15][CH2:20][CH2:19][C:18]([F:23])([F:22])[F:17])[O:10][C:9]=2[CH:16]=1)(=[O:3])=[O:4]

참가 물질

4

반응물 2

HCID 1561651,1,1-Trifluoro-3-iodopropaneHCID 66878351[(2S)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methylamine

생성물 1

HCID 44470013N-{[(2S)-7-(Methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methyl}-N-(3,3,3-trifluoropropyl)amine

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
120 °C

실험 절차

A mixture of [(2S)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methylamine (0.31 g, 1.27 mmol), 1,1,1-trifluoro-3-iodopropane (0.16 ml, 1.4 mmol) K2CO3 (0.35 g, 2.5 mmol) and ACN (4 ml) was heated under microwave radiation at 120° C. for 40 min. The product was evaporated to dryness and was purified by preparative HPLC (MeOH/NH3 buffer). Yield: 0.19 g, 44%. The amine was converted to the hydrochloric acid salt and was crystallized from MeOH/Et2O. M.p. 204° C. MS m/z (rel. intensity, 70 eV) 339 (M+, 3), 127 (5), 126 (bp), 79 (4), 51 (4). [α]=−52° (MeOH).

후처리

  1. customThe product was evaporated to dryness
  2. customwas purified by preparative HPLC (MeOH/NH3 buffer)
  3. customwas crystallized from MeOH/Et2O
  4. custom[α]=−52° (MeOH)

출처 및 근거

ORD 기록
ord-b5a4e5da5b324af78e2d58cb3e81d15b
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524766B2

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