Potassium hydroxy sulfite → HCID 178488249, compound

HRID 639392Notes

Reaction equation

HRID 639392 reaction equation
OO[S:3]([O-:5])=O.[K+].S1[C:11]2[CH:12]=[C:13]([NH:16][C:17]3[N:22]=[C:21]([C:23]4[C:24]([C:28]5[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([O:35][CH3:36])[CH:29]=5)=[N:25][NH:26][CH:27]=4)[CH:20]=[CH:19][N:18]=3)[CH:14]=[CH:15][C:10]=2[N:9]=[CH:8]1>O.CO>[Cl:34][C:31]1[CH:32]=[CH:33][C:28]([C:24]2[C:23]([C:21]3[CH:20]=[CH:19][N:18]=[C:17]([NH:16][C:13]4[CH:14]=[CH:15][C:10]5[N:9]=[CH:8][S:3](=[O:5])[C:11]=5[CH:12]=4)[N:22]=3)=[CH:27][NH:26][N:25]=2)=[CH:29][C:30]=1[O:35][CH3:36]

Participants

5

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 178488250HCID 178488250, compound

Product 1

HCID 178488249HCID 178488249, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of OXONE (=KHSO5; 141.4 mg, 0.23 mmoles) in water (2 mL) is added dropwise to a suspension of benzothiazol-6-yl-{4-[3-(4-chloro-3-methoxy-phenyl)-1H-pyrazol-4-yl]-pyrimidin-2-yl}-amine (Example 44) (20 mg, 0.046 mmoles) in methanol (2 mL) at rt. After stirring overnight at rt the suspension is diluted with water upon which the suspension turns to a clear yellow solution. The reaction mixture is extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate, concentrated and chromatographed on SiO2 (5% MeOH/CH2Cl2) to yield the title compound as light yellow solid: ES-MS 451.0751 [M+H]; single peak at tR=4.93 min (System 3).

Workup

  1. extractionThe reaction mixture is extracted with ethyl acetate
  2. dry with materialThe combined organic phases are dried over sodium sulfate
  3. concentrationconcentrated
  4. customchromatographed on SiO2 (5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-91d71723dba24210b9f4c709fb583693
Source dataset
uspto-grants-2010_04
Patent number
US07691855B2

Reaction notes

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