Hydrochloric Acid → HCID 46832785, compound

HRID 1818808Notes

Reaction equation

HRID 1818808 reaction equation
[F:1][C:2]([F:26])([CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])[S:9]1(=[O:25])=[O:24])[C:3]([NH:5][CH3:6])=O.B.O1CCCC1.[ClH:33]>C(OCC)C>[ClH:33].[F:26][C:2]([F:1])([CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])[S:9]1(=[O:24])=[O:25])[CH2:3][NH:5][CH3:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 68713994HCID 68713994, compound

Product 1

HCID 46832785HCID 46832785, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 2,2-difluoro-3-[3-(2-fluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]-N-methylpropanamide (ca. 1 mmol) at 0° C., was added borane-tetrahydrofuran complex (1 M in THF, 3 mL, 3 mmol). After stirring for 2 h, the mixture was quenched with dilute hydrochloric acid, basified (2 N NaOH) and extracted with ethylacetate. The organic layer was washed with water, dried (MgSO4) and evaporated. The residue was purified by silica gel column chromatography (hexanes: ethylacetate, gradient elution) to afford the crude product which was further purified by reverse phase hplc (Xterra RP18 19×150 mm, 5 u, 55% MeOH 45% H2O w/0.05% NH4OH, 20 mL/min). The residue obtained was dissolved in diethyl ether, treated with excess ethereal HCl and lyophilized to afford 2,2-difluoro-3-[3-(2-fluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]-N-methylpropan-1-amine hydrochloride as a white solid.

Workup

  1. customthe mixture was quenched with dilute hydrochloric acid
  2. extractionextracted with ethylacetate
  3. washThe organic layer was washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography (hexanes: ethylacetate, gradient elution)
  7. customto afford the crude product which
  8. customwas further purified by reverse phase hplc (Xterra RP18 19×150 mm, 5 u, 55% MeOH 45% H2O w/0.05% NH4OH, 20 mL/min)
  9. customThe residue obtained

Sources & evidence

ORD record
ord-14ca2db1300f4637a6579b7a9bb068b3
Source dataset
uspto-grants-2009_10
Patent number
US07601722B2

Reaction notes

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