1,1,1-Trifluoro-3-iodopropane → N-{[(2S)-5-Fluoro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methyl}-N-(3,3,3-trifluoropropyl)amine

HRID 38925

Reaction equation

HRID 38925 reaction equation
[F:1][C:2]1[C:11]2[O:10][CH2:9][C@H:8]([CH2:12][NH2:13])[O:7][C:6]=2[CH:5]=[C:4]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:3]=1.[F:18][C:19]([F:24])([F:23])[CH2:20][CH2:21]I>C(#N)C>[F:1][C:2]1[C:11]2[O:10][CH2:9][C@H:8]([CH2:12][NH:13][CH2:21][CH2:20][C:19]([F:24])([F:23])[F:18])[O:7][C:6]=2[CH:5]=[C:4]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:3]=1

Participants

4

Reactant 2

HCID 1561651,1,1-Trifluoro-3-iodopropaneHCID 67198473[(2S)-5-Fluoro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methylamine

Product 1

HCID 44470012N-{[(2S)-5-Fluoro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methyl}-N-(3,3,3-trifluoropropyl)amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1-[(2S)-5-fluoro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methaneamine (0.3 g, 1.1 mmol), 1,1,1-trifluoro-3-iodopropane (0.16 ml, 1.4 mmol) K2CO3 (0.32 g, 2.3 mmol) and ACN (4 ml) was heated under microwave radiation at 120° C. for 30 min. The mixture was filtrated and evaporated to dryness and the product was purified by flash column chromatography (EtOAc). Yield: 0.12 g, 31%. The amine was converted to the hydrochloric acid salt and crystallized from MeOH/Et2O. M.p. 233° C. MS m/z (rel. intensity, 70 eV) 357 (M+, 1), 274 (3), 127 (5), 126 (bp), 69 (3). [α]=−53° (MeOH).

Workup

  1. filtrationThe mixture was filtrated
  2. customevaporated to dryness
  3. customthe product was purified by flash column chromatography (EtOAc)
  4. customcrystallized from MeOH/Et2O
  5. custom[α]=−53° (MeOH)

Sources & evidence

ORD record
ord-a2a7245bab0f480fbf5c11acfc863f3a
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Linked notes

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