Hydrochloric Acid → 3-[6-fluoro-1-(2-fluorophenyl)-2,2-dioxido-1,4-dihydro-3H-2,1,3-benzothiadiazin-3-yl]-N-methylpropan-1-amine

HRID 2237502Notes

Reaction equation

HRID 2237502 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][C:9]2[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:8]=2[N:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])[S:6]1(=[O:24])=[O:23].[CH3:25][NH2:26].Cl>>[F:15][C:12]1[CH:13]=[CH:14][C:8]2[N:7]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[F:22])[S:6](=[O:24])(=[O:23])[N:5]([CH2:4][CH2:3][CH2:2][NH:26][CH3:25])[CH2:10][C:9]=2[CH:11]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 685819023-(3-bromopropyl)-6-fluoro-1-(2-fluorophenyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide

Product 1

HCID 250300333-[6-fluoro-1-(2-fluorophenyl)-2,2-dioxido-1,4-dihydro-3H-2,1,3-benzothiadiazin-3-yl]-N-methylpropan-1-amineYield 68%

Procedure

In an analogous manner to Example 111 step 5, 3-(3-bromopropyl)-6-fluoro-1-(2-fluorophenyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide (0.1 g, 0.25 mmol) was reacted to methylamine and then treated with HCl to provide 3-[6-fluoro-1-(2-fluorophenyl)-2,2-dioxido-1,4-dihydro-3H-2,1,3-benzothiadiazin-3-yl]-N-methylpropan-1-amine (0.102 g, 68%) as a white solid:

Sources & evidence

ORD record
ord-2fa8db84963443918bde5eb692076585
Source dataset
uspto-grants-2010_05
Patent number
US07718652B2

Reaction notes

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