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

HRID 2237497Notes

Reaction equation

HRID 2237497 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[N:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])[S:7]1(=[O:24])=[O:23].[CH:25]1([NH2:28])[CH2:27][CH2:26]1.Cl>>[F:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[N:8]1[C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[CH2:11][N:6]([CH2:5][CH2:4][CH2:3][CH2:2][NH:28][CH:25]2[CH2:27][CH2:26]2)[S:7]1(=[O:24])=[O:23]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 69828CyclopropylamineHCID 685821143-(4-bromobutyl)-1-(2-fluorophenyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide

Product 1

HCID 25030030N-{4-[1-(2-fluorophenyl)-2,2-dioxido-1,4-dihydro-3H-2,1,3-benzothiadiazin-3-yl]butyl}cyclopropanamineYield 92%

Procedure

In an analogous manner to Example 11 step 5, 3-(4-bromobutyl)-1-(2-fluorophenyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide (0.11 g, 0.26 mmol) was reacted to cyclopropylamine and then treated with HCl to provide N-{4-[1-(2-fluorophenyl)-2,2-dioxido-1,4-dihydro-3H-2,1,3-benzothiadiazin-3-yl]butyl}cyclopropanamine (0.099 g, 92%) as a white solid:

Sources & evidence

ORD record
ord-5549066cce024e95a3f8b7c72c95a079
Source dataset
uspto-grants-2010_05
Patent number
US07718652B2

Reaction notes

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