Ammonium Chloride → HCID 21186338, compound

HRID 361440Notes

Reaction equation

HRID 361440 reaction equation
[Li+].[AlH4-].[O:3]1[CH2:38][C:4]1([CH3:39])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:17]([S:18]([N:21](C(OCC(C)C)=O)[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.[Cl-].[NH4+]>CCOCC.C1COCC1>[OH:3][C:4]([CH3:39])([CH3:38])[CH2:5][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

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 28112Lithium aluminum hydrideHCID 21186241HCID 21186241, compound

Product 1

HCID 21186338HCID 21186338, compoundYield 7.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium tetrahydridoaluminate (20.5 ml of a 1M solution in ether) was added over 10 minutes to a solution of 2-[4-(2,3-epoxy-2-methylpropyl)phenyl]-N-(isobutoxycarbonyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (1.8 g) in anhydrous THF at 0° C. After 30 minutes the reaction mixture was poured into saturated aqueous ammonium chloride solution (50 ml) and was extracted with ethyl acetate (4×50 ml). The extracts were washed with brine and dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by gradient elution with 0-80% ethyl acetate/hexane through a silica gel Mega Bond Elut column to give 2-[4-(2-hydroxy-2-methylpropyl)phenyl]-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (0.115 g) as a foam; 1H NMR (CDCl3 +CD3COOD): 1.3 (s, 6 H), 2.3 (s, 3 H), 2.8 (s, 2 H), 3.8 (s, 3 H), 7.2-7.3 (m, 5 H), 7.55 (dd, 1 H), 8.7 (dd, 1 H), 8.85 (dd, 1 H); mass spectrum (+ve ESP): 429 (M+H)+.

Workup

  1. extractionwas extracted with ethyl acetate (4×50 ml)
  2. washThe extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. customVolatile material was removed by evaporation
  5. customthe residue was purified by gradient elution with 0-80% ethyl acetate/hexane through a silica gel Mega Bond Elut column

Sources & evidence

ORD record
ord-83ac28e01d834df9b8bc943d3df0f47f
Source dataset
uspto-grants-1999_02
Patent number
US05866568

Reaction notes

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