Methylamine → 3-[3-(2-fluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]-N-methylbutan-1-amine

HRID 1818788Notes

Reaction equation

HRID 1818788 reaction equation
Br[CH2:2][CH2:3][CH:4]([N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])[S:7]1(=[O:23])=[O:22])[CH3:5].[CH3:24][NH2:25]>>[F:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[N:8]1[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:6]([CH:4]([CH3:5])[CH2:3][CH2:2][NH:25][CH3:24])[S:7]1(=[O:22])=[O:23]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 687098281-(3-Bromo-1-methylpropyl)-3-(2-fluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide

Product 1

HCID 249378893-[3-(2-fluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]-N-methylbutan-1-amine

Procedure

1-(3-bromo-1-methylpropyl)-3-(2-fluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (0.04 g, 0.09 mmol) was dissolved in 2 mL of MeNH2 solution (8M in EtOH). The solution was irradiated in a microwave cuvette at 100° C. for 3 minutes. The reaction mixture was concentrated then loaded directly onto silica gel and purified via Isco chromatography (Redisep, silica, gradient 0-10% 7M ammonia/MeOH solution in dichloromethane) to afford 44 mg of 3-[3-(2-fluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]-N-methylbutan-1-amine.

Workup

  1. customThe solution was irradiated in a microwave cuvette at 100° C. for 3 minutes
  2. concentrationThe reaction mixture was concentrated
  3. custompurified via Isco chromatography (Redisep, silica, gradient 0-10% 7M ammonia/MeOH solution in dichloromethane)

Sources & evidence

ORD record
ord-4324c09940054289a5e4c9956a371b66
Source dataset
uspto-grants-2009_10
Patent number
US07601722B2

Reaction notes

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