Water → HCID 136346629, compound

HRID 556358Notes

Reaction equation

HRID 556358 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]3[C:22]4[CH:23]=[CH:24][C:25]([O:27]C)=[CH:26][C:21]=4[S:20][N:19]=3)=[O:17])=[CH:11][C:10]=2[C:29]([F:32])([F:31])[F:30])[CH2:4][CH2:3]1.B(Br)(Br)Br.O.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.CCOC(C)=O>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]3[C:22]4[CH:23]=[CH:24][C:25]([OH:27])=[CH:26][C:21]=4[S:20][N:19]=3)=[O:17])=[CH:11][C:10]=2[C:29]([F:32])([F:30])[F:31])[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 25134Boron tribromideHCID 669928876-Methoxy-benzo[d]isothiazole-3-carboxylic acid [4-(4-methyl-piperazin-1-ylmethyl)-3-trifluoromethyl-phenyl]-amide

Product 1

HCID 136346629HCID 136346629, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.923 g (4.14 mMol) 6-methoxy-benzo[d]isothiazole-3-carboxylic acid [4-(4-methyl-piperazin-1-ylmethyl)-3-trifluoromethyl-phenyl]-amide in 120 ml of a 1 M solution of BBr3 in CH2Cl2 are stirred for 16 h at 45° C. Then the solution is poured into water and EtOAc, the aq. layer is neutralized with Na2CO3, separated off and extracted twice with EtOAc. The organic layers are washed twice with water and brine, dried (Na2SO4) and concentrated. Reversed phase chromatography (Gilson system) gives the title compound: MS: [M−1]=451; HPLC: tRet=11.6.

Workup

  1. customseparated off
  2. extractionextracted twice with EtOAc
  3. washThe organic layers are washed twice with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1f714be5457542928f0e0284de6a2e20
Source dataset
uspto-grants-2011_11
Patent number
US08058276B2

Reaction notes

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