Hydrochloric Acid → HCID 44251416, compound

HRID 38910Notes

Reaction equation

HRID 38910 reaction equation
CC1C=CC(S(O[CH2:12][C@@H:13]2[O:18][C:17]3[CH:19]=[C:20]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:21]=[C:22]([F:23])[C:16]=3[O:15][CH2:14]2)(=O)=O)=CC=1.[CH2:28]([NH2:30])[CH3:29].Cl>C(#N)C>[F:23][C:22]1[C:16]2[O:15][CH2:14][C@H:13]([CH2:12][NH:30][CH2:28][CH3:29])[O:18][C:17]=2[CH:19]=[C:20]([S:24]([CH3:27])(=[O:25])=[O:26])[CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6341EthylamineHCID 86652937[(2R)-5-fluoro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate

Product 1

HCID 44251416HCID 44251416, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Preparation according to Example 5 using [(2R)-5-fluoro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate (0.56 g, 1.33 mmol), ethanamine (1 ml, 70% in water) and ACN (3 ml). Yield: 0.32 g, 83%. The amine was converted to the hydrochloric acid salt and crystallized from MeOH/Et2O. M.p. 274° C. MS m/z (rel. intensity, 70 eV) 289 (M+, 3), 70 (3), 59 (4), 58 (bp), 56 (3). [α]=−58° (MeOH).

Workup

  1. customPreparation
  2. customcrystallized from MeOH/Et2O
  3. custom[α]=−58° (MeOH)

Sources & evidence

ORD record
ord-b1516aa20233412283400fce2135870e
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

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