Methylamine → HCID 44468376, compound

HRID 38959Notes

Reaction equation

HRID 38959 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]([Cl:23])[C:16]=3[O:15][CH2:14]2)(=O)=O)=CC=1.[CH3:28][NH2:29]>C(#N)C>[Cl:23][C:22]1[C:16]2[O:15][CH2:14][C@H:13]([CH2:12][NH:29][CH3:28])[O:18][C:17]=2[CH:19]=[C:20]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:21]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 86652939[(2R)-5-chloro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate

Product 1

HCID 44468376HCID 44468376, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of [(2R)-5-chloro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate (0.48 g, 1.1 mmol), methanamine (1.5 ml, 33% in EtOH, 4 mmol) and ACN (3 ml) was heated under microwave radiation at 120° C. for 20 min. Purification on SCX-3 column (TEA/MeOH) and by flash column chromatography (MeOH/EtOAc) gave the title compound (0.18 g). The amine was converted to the hydrochloric acid salt and crystallized from MeOH/Et2O. M.p. 262° C. MS m/z (rel. intensity, 70 eV) 291 (M+, 43), 113 (57), 85 (80), 70 (bp), 63 (84), 50 (60) [α]=−61° (MeOH).

Workup

  1. customPurification on SCX-3 column (TEA/MeOH)

Sources & evidence

ORD record
ord-98c92b8795d844bdb3ba044769f2da92
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

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