Sodium borohydride → HCID 22612045, compound

HRID 844046Notes

Reaction equation

HRID 844046 reaction equation
[C:1]([C:4]1[S:8][C:7]([CH2:9][NH:10][C:11](=[O:25])[C:12]2[CH:17]=[CH:16][CH:15]=[N:14][C:13]=2[O:18][C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>C(Cl)Cl.O1CCCC1>[OH:3][CH:1]([C:4]1[S:8][C:7]([CH2:9][NH:10][C:11](=[O:25])[C:12]2[CH:17]=[CH:16][CH:15]=[N:14][C:13]=2[O:18][C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 22612210HCID 22612210, compound

Product 1

HCID 22612045HCID 22612045, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of N-(5-Acetyl-thiophen-2-ylmethyl)-2-(pyridin-3-yloxy)-nicotinamide (0.300 grams, 0.85 mmole) in methylene chloride (25 ml) and tetrahydrofuran (25 ml) at room temperature was added sodium borohydride (0.035 grams, 0.93 mmole) and stirred for 2 hours. The mixture was quenched with saturated NH4Cl (˜1 ml) and concentrated under reduced pressure to about 15 ml. This mixture was poured into water and extracted with ethyl acetate. The combined organics were washed with water and brine, dried over MgSO4, filtered and concentrated to give an oil that was purified by chromatography on silica eluting with 5% methanol/methylene chloride. Recrystalization from ethyl acetate/hexane gave a white solid. (0.207 g). M.P. 92-94° C.; Anal. calcd. for C18H17N3O3S: C, 60.83;H, 4.82; N, 11.82. Found: C, 60.68; H, 4.77; N, 11.89.

Workup

  1. customThe mixture was quenched with saturated NH4Cl (˜1 ml)
  2. concentrationconcentrated under reduced pressure to about 15 ml
  3. additionThis mixture was poured into water
  4. extractionextracted with ethyl acetate
  5. washThe combined organics were washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give an oil that
  10. customwas purified by chromatography on silica eluting with 5% methanol/methylene chloride
  11. customRecrystalization from ethyl acetate/hexane
  12. customgave a white solid

Sources & evidence

ORD record
ord-55a43cc57b2247fa97fa230bf5e4f372
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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