Potassium hydroxy sulfite → HCID 57725447, compound

HRID 1922284Notes

Reaction equation

HRID 1922284 reaction equation
OO[S:3]([O-:5])=O.[K+].[OH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[NH:14][C:15]1S[C:17]2[CH:23]=[C:22]([O:24][C:25]3[CH:30]=[CH:29][N:28]=[C:27]([C:31]([NH:33][CH3:34])=[O:32])[CH:26]=3)[CH:21]=[CH:20][C:18]=2[N:19]=1>O.CO>[OH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[NH:14][C:15]1[S:3](=[O:5])[C:20]2[CH:21]=[C:22]([O:24][C:25]3[CH:30]=[CH:29][N:28]=[C:27]([C:31]([NH:33][CH3:34])=[O:32])[CH:26]=3)[CH:23]=[CH:17][C:18]=2[N:19]=1

Participants

5

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 461849864-((2-(((1R,2R)-2-hydroxycyclohexyl)aMino)benzo[d]thiazol-6-yl)oxy)-N-MethylpicolinaMide

Product 1

HCID 57725447HCID 57725447, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of OXONE® (KHSO5, 380 mg, mmol) in water (4 ml) was added dropwise to a solution of 4-(2-((1R,2R)-2-hydroxycyclohexylamino)benzo[d]thiazol-6-yloxy)-N-methylpicolinamide (25 mg, mmol) in methanol (4 ml) at rt. After stirring for 23 hours the suspension is diluted with water (50 ml) and extracted with ethyl acetate (2×10 ml). The combined organic layers were washed with brine, concentrated, and purified by prep HPLC to yield the title compound as white solid. Yield: 2.4 mg. ES/MS m/z 415.1 (MH+), Rt=1.81 min.

Workup

  1. extractionextracted with ethyl acetate (2×10 ml)
  2. washThe combined organic layers were washed with brine
  3. concentrationconcentrated
  4. custompurified by prep HPLC

Sources & evidence

ORD record
ord-4bed5f76498f4f16873b810e2cd2b570
Source dataset
uspto-grants-2012_05
Patent number
US08173689B2

Reaction notes

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