Hydrochloric Acid → HCID 22504887, compound

HRID 1814170Notes

Reaction equation

HRID 1814170 reaction equation
C[O:2][C:3](=[O:28])[CH2:4][O:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([S:14][CH2:15][CH2:16][C:17](=O)[N:18]([CH3:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:8][C:7]=1[CH3:27].O=P(Cl)(Cl)Cl.[BH4-].[Na+].Cl.C(=O)(O)[O-].[Na+]>>[CH3:13][O:12][C:10]1[C:9]([S:14][CH2:15][CH2:16][CH2:17][N:18]([CH3:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:8][C:7]([CH3:27])=[C:6]([CH:11]=1)[O:5][CH2:4][C:3]([OH:28])=[O:2]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 20770840HCID 20770840, compound

Product 1

HCID 22504887HCID 22504887, compound

Procedure

Compound 63A was dissolved POCl3 (250 mg, 1.6 mmol) and stirred for 15 minutes. The reaction was concentrated by blowing with nitrogen followed by concentration under vacuum. The intermediate was dissolved in 5 ml dimethoxyethane and cooled to ca. 5 C. Sodium borohydride (20 mg, 0.53 mmol) was added followed by warming to room temp. After 3 h 25 ml 2N HCl was added and heated to boiling for 1 minute. Saturated sodium bicarbonate was added to pH ca. 7-8. The crude product was extracted with 2×20 ml ethyl acetate, dried over anhydrous sodium sulfate, decanted and concentrated. Liquid chromatography gave the title product as a clear colorless oil. MS m/z 391 (M+1). Step 4. Preparation of {5-Methoxy-2-methyl-4-[3-(methyl-pyridin-2-yl-amino)-propylsulfanyl]-phenoxy}-acetic acid (Compound 63)

Workup

  1. concentrationThe reaction was concentrated
  2. concentrationfollowed by concentration under vacuum
  3. dissolutionThe intermediate was dissolved in 5 ml dimethoxyethane
  4. temperaturecooled to ca. 5 C
  5. temperatureheated
  6. waitto boiling for 1 minute
  7. extractionThe crude product was extracted with 2×20 ml ethyl acetate
  8. dry with materialdried over anhydrous sodium sulfate
  9. customdecanted
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-753744b937574d1b8ab0eabaa86c8fb2
Source dataset
uspto-grants-2005_04
Patent number
US06875780B2

Reaction notes

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