Methylamine → 2-[1-(2-fluorophenyl)-2,2-dioxido-1,4-dihydro-3H-2,1,3-benzothiadiazin-3-yl]-N-methylethanamine

HRID 2237490Notes

Reaction equation

HRID 2237490 reaction equation
Br[CH2:2][CH2:3][N:4]1[CH2:9][C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[N:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])[S:5]1(=[O:22])=[O:21].[CH3:23][NH2:24]>C(O)C>[F:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[N:6]1[C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[CH2:9][N:4]([CH2:3][CH2:2][NH:24][CH3:23])[S:5]1(=[O:22])=[O:21]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 685822933-(2-bromoethyl)-1-(2-fluorophenyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide

Product 1

HCID 250297922-[1-(2-fluorophenyl)-2,2-dioxido-1,4-dihydro-3H-2,1,3-benzothiadiazin-3-yl]-N-methylethanamineYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(2-bromoethyl)-1-(2-fluorophenyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide (0.96 g, 0.25 mmol) was dissolved in an 8 M solution of methylamine in ethanol (4 ml) and was stirred in a capped vial at room temperature for two hours. The reaction mixture was evaporated and the residue purified by flash chromatography (SiO2, 0-5% 7 M NH3-methanol/dichloromethane). The purified free-base was dissolved in dichloromethane (3 mL) and treated with hydrogen chloride (1.0 mL of a 2 M solution in ethyl ether), resulting in a white precipitate that was evaporated and dried under vacuum to afford 2-[1-(2-fluorophenyl)-2,2-dioxido-1,4-dihydro-3H-2,1,3-benzothiadiazin-3-yl]-N-methylethanamine (0.071 g, 85%) as a white solid:

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue purified by flash chromatography (SiO2, 0-5% 7 M NH3-methanol/dichloromethane)
  3. dissolutionThe purified free-base was dissolved in dichloromethane (3 mL)
  4. additiontreated with hydrogen chloride (1.0 mL of a 2 M solution in ethyl ether),
  5. customresulting in a white precipitate that
  6. customwas evaporated
  7. customdried under vacuum

Sources & evidence

ORD record
ord-79ccb5368a334cf58cdb5130eb66fe11
Source dataset
uspto-grants-2010_05
Patent number
US07718652B2

Reaction notes

Loading…