Dimethylamine → HCID 57886246, compound

HRID 1818824Notes

Reaction equation

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

Participants

Reactant 2

HCID 674Dimethylamine

HCID 68711215HCID 68711215, compound

Product 1

HCID 57886246HCID 57886246, compoundYield 92%

Procedure

In an analogous manner to general procedure V, 1-[4-(bromomethyl)benzyl]-3-(2-fluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole2,2-dioxide (0.11 g, 0.24 mmol) was treated with dimethylamine (10 mL) to provide 0.09 g, (92%) of 1-(4-{[3-(2-fluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]methyl}phenyl)-N,N-dimethylmethanamine. MS (ES) m/z 411.0. HPLC purity 97.3% 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-a4114fb499f240baae6e1cedc967ddf6
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601722B2

Reaction notes

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