Dimethylamine → 1-(3-{[3-(2-fluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]methyl}phenyl)-N,N-dimethylmethanamine

HRID 1818823Notes

Reaction equation

HRID 1818823 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][CH:27]=1)[CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])[S:8]1(=[O:24])=[O:23].[CH3:28][NH:29][CH3:30]>>[F:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[N:9]1[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:7]([CH2:6][C:5]2[CH:4]=[C:3]([CH2:2][N:29]([CH3:30])[CH3:28])[CH:27]=[CH:26][CH:25]=2)[S:8]1(=[O:24])=[O:23]

Participants

3

Reactant 2

HCID 674DimethylamineHCID 687116231-[3-(Bromomethyl)benzyl]-3-(2-fluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide

Product 1

HCID 578863481-(3-{[3-(2-fluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]methyl}phenyl)-N,N-dimethylmethanamineYield 39%

Procedure

In an analogous manner to general procedure V, 1-[3-(bromomethyl)benzyl]-3-(2-fluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole2,2-dioxide (0.07 g, 0.18 mmol) was treated with dimethylamine (10 mL) to provide 0.03 g (39%) of 1-(3-{[3-(2-fluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]methyl}phenyl)-N,N-dimethylmethanamine. HRMS: calcd for C22H22FN3O2S+H+, 412.14895; found (ESI, [M+H]+), 412.1493; HPLC purity 96.3% at 210-370 nm, 7.7 min.; Xterra RP18, 3.5 u, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. Ph=3.5/ACN+MeOH) for 10 min, hold 4 min.

Sources & evidence

ORD record
ord-8eb4c3fdbe534b48baa0e902f52d2074
Source dataset
uspto-grants-2009_10
Patent number
US07601722B2

Reaction notes

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