Hydrochloric Acid → 3-[3-(2,3-difluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]-N-methyl-1-phenylpropan-1-amine

HRID 1818799Notes

Reaction equation

HRID 1818799 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]([CH2:18][CH2:19][CH:20]([N:27](C)[C:28](=O)OC(C)(C)C)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[S:10]1(=[O:37])=[O:36].Cl>CCOCC>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]([CH2:18][CH2:19][CH:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:27][CH3:28])[S:10]1(=[O:36])=[O:37]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86621285tert-butyl {3-[3-(2,3-difluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]-1-phenylpropyl}methylcarbamate

Product 1

HCID 249377583-[3-(2,3-difluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]-N-methyl-1-phenylpropan-1-amineYield 79.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

tert-butyl {3-[3-(2,3-difluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]-1-phenylpropyl}methylcarbamate (0.10 g, 0.19 mmol) was treated with an excess of 2N HCl in ether. The precipitated amine salt was collected to give 65 mg of 3-[3-(2,3-difluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]-N-methyl-1-phenylpropan-1-amine.

Workup

  1. customThe precipitated amine salt was collected

Sources & evidence

ORD record
ord-dd0a18c0c9544581ae677b4055f4cde1
Source dataset
uspto-grants-2009_10
Patent number
US07601722B2

Reaction notes

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