Hydrochloric Acid → N-{2-[6-fluoro-1-(2-fluorophenyl)-2,2-dioxido-1,4-dihydro-3H-2,1,3-benzothiadiazin-3-yl]ethyl}cyclopropanamine

HRID 2237500Notes

Reaction equation

HRID 2237500 reaction equation
Br[CH2:2][CH2:3][N:4]1[CH2:9][C:8]2[CH:10]=[C:11]([F:14])[CH:12]=[CH:13][C:7]=2[N:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])[S:5]1(=[O:23])=[O:22].[CH:24]1([NH2:27])[CH2:26][CH2:25]1.Cl>>[F:14][C:11]1[CH:12]=[CH:13][C:7]2[N:6]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[F:21])[S:5](=[O:23])(=[O:22])[N:4]([CH2:3][CH2:2][NH:27][CH:24]3[CH2:26][CH2:25]3)[CH2:9][C:8]=2[CH:10]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 69828CyclopropylamineHCID 685835933-(2-bromoethyl)-6-fluoro-1-(2-fluorophenyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide

Product 1

HCID 25030032N-{2-[6-fluoro-1-(2-fluorophenyl)-2,2-dioxido-1,4-dihydro-3H-2,1,3-benzothiadiazin-3-yl]ethyl}cyclopropanamineYield 95%

Procedure

In an analogous manner to Example 11 step 5, 3-(2-bromoethyl)-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 cyclopropylamine and then treated with HCl to provide N-{2-[6-fluoro-1-(2-fluorophenyl)-2,2-dioxido-1,4-dihydro-3H-2,1,3-benzothiadiazin-3-yl]ethyl}cyclopropanamine (0.099 g, 95%) as a white solid:

Sources & evidence

ORD record
ord-58834da571a8481d9e3a133f9d1bc8a9
Source dataset
uspto-grants-2010_05
Patent number
US07718652B2

Reaction notes

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