Sodium Bicarbonate → [4-(1H-benzoimidazole-2-sulfonyl)-butyl]-(3,5-dimethyl-pyridin-2-ylmethyl)-amine

HRID 1592463Notes

Reaction equation

HRID 1592463 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10]([CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])(=[O:12])=[O:11].[CH3:18][C:19]1[C:20]([CH:26]=O)=[N:21][CH:22]=[C:23]([CH3:25])[CH:24]=1.[BH4-].[Na+].C([O-])(O)=O.[Na+]>CO.C(Cl)Cl>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10]([CH2:13][CH2:14][CH2:15][CH2:16][NH:17][CH2:26][C:20]1[C:19]([CH3:18])=[CH:24][C:23]([CH3:25])=[CH:22][N:21]=1)(=[O:12])=[O:11]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 187316833,5-Dimethylpyridine-2-carbaldehydeHCID 672726254-(1H-benzoimidazole-2-sulfonyl)-butylamine

Product 1

HCID 67273026[4-(1H-benzoimidazole-2-sulfonyl)-butyl]-(3,5-dimethyl-pyridin-2-ylmethyl)-amineYield 14%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(1H-benzoimidazole-2-sulfonyl)-butylamine (350 mg, 1.4 mmol) and 3,5-dimethylpyridine-2-carbaldehyde (187 mg, 1.4 mmol) in dry MeOH (10 mL) was stirred for 3 h. At this time, solid NaBH4 (116 mg, 4.2 mmol) was added in one portion. Stirring was continued for 1 h, then saturated aqueous NaHCO3 (10 mL) and CH2Cl2 (20 mL) was added. The biphasic mixture was extracted with CH2Cl2 (3×20 mL), then the combined organic fractions were dried (MgSO4), and concentrated. Purification of the crude material by flash chromatography (silica gel, CH2Cl2/MeOH/NH4OH; 20:2:1) afforded 70 mg of [4-(1H-benzoimidazole-2-sulfonyl)-butyl]-(3,5-dimethyl-pyridin-2-ylmethyl)-amine (14% yield). 1H NMR (CDCl3) δ 184-1.86 (m, 4H), 2.26 (s, 3H), 2.29 (s, 3H), 2.95-3.00 (m, 2H), 3.34-3.56 (m, 2H), 4.12 (s, 2H), 7.34-7.37 (m, 2H), 7.44 (s, 1H), 7.67-7.71 (m, 2H), 8.19 (s, 1H).

Workup

  1. extractionThe biphasic mixture was extracted with CH2Cl2 (3×20 mL)
  2. dry with materialthe combined organic fractions were dried (MgSO4)
  3. concentrationconcentrated
  4. customPurification of the crude material by flash chromatography (silica gel, CH2Cl2/MeOH/NH4OH; 20:2:1)

Sources & evidence

ORD record
ord-db0cd1370ef5444ea5e0289a7ffa9e46
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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