Hydrochloric Acid → HCID 21186258, compound

HRID 1107478Notes

Reaction equation

HRID 1107478 reaction equation
[BH4-].[Na+].[C:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:17]([S:18]([NH:21][C:22]3[C:27]([O:28][CH3:29])=[N:26][C:25]([CH3:30])=[CH:24][N:23]=3)(=[O:20])=[O:19])=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:8][CH:7]=1)(=[O:5])[CH3:4].O.Cl>C(O)C>[OH:5][CH:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:17]([S:18]([NH:21][C:22]3[C:27]([O:28][CH3:29])=[N:26][C:25]([CH3:30])=[CH:24][N:23]=3)(=[O:20])=[O:19])=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:8][CH:7]=1)[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 21186292HCID 21186292, compound

Product 1

HCID 21186258HCID 21186258, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium tetrahydridoborate (0.051 g) was added portionwise over 5 minutes to a solution of 2-(4-acetylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (0.135 g) in ethanol (5 ml). The mixture was stirred for 45 minutes at ambient temperature and was then poured into water (20 ml) and acidified to pH 3 with 2M hydrochloric acid. The mixture was extracted with ethyl acetate (3×20 ml). The extracts were combined, washed with water and saturated sodium chloride solution and dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by gradient elution with 10-70% ethyl acetate/hexane through a silica gel Mega Bond Elut column to give 2-[4-(1-hydroxyethyl)phenyl]-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (0.096 g) as a foam; 1H NMR (CDCl3 +CD3COOD): 1.55 (d, 3H), 2.3 (s, 3H), 3.85 (s, 3H) 4.95 (q, 1H), 7.25 (s, 1H), 7.3 (d, 2H), 7.35 (d, 2H), 7.55 (dd, 1H), 8.7 (d, 1H), 8.85 (d, 1H); mass spectrum (+ve ESP): 401 (M+H)+.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×20 ml)
  2. washwashed with water and saturated sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. customVolatile material was removed by evaporation
  5. customthe residue was purified by gradient elution with 10-70% ethyl acetate/hexane through a silica gel Mega Bond Elut column

Sources & evidence

ORD record
ord-c22d50a9dc14470ab6f855be3df43190
Source dataset
uspto-grants-2000_05
Patent number
US06060475

Reaction notes

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