Methanol → HCID 178440775, compound

HRID 1595409Notes

Reaction equation

HRID 1595409 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=3)=[N:10][C:9]=2[C:23]([NH:25][C:26]2[S:27][CH:28]=[CH:29][N:30]=2)=[O:24])=[CH:4][CH:3]=1.CO.[CH:33](=O)[CH2:34][CH2:35][CH2:36][CH:37]=O.C([BH3-])#N.[Na+]>O1CCCC1.O>[C:19]([C:16]1[CH:15]=[CH:14][C:13]([C:11]2[NH:12][C:8]([C:5]3[CH:4]=[CH:3][C:2]([N:1]4[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]4)=[CH:7][CH:6]=3)=[C:9]([C:23]([NH:25][C:26]3[S:27][CH:28]=[CH:29][N:30]=3)=[O:24])[N:10]=2)=[CH:18][CH:17]=1)([CH3:22])([CH3:20])[CH3:21]

Participants

7

Reactant 4

HCID 887MethanolHCID 3485GlutaraldehydeHCID 5003444Sodium cyanoborohydrideHCID 178440776HCID 178440776, compound

Product 1

HCID 178440775HCID 178440775, compoundYield 10.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-(4-Aminophenyl)-2-(4-tert-butylphenyl)-N-(2-thiazolyl)-imidazole-4-carboxamide (1.0 g) obtained in Example 77 was dissolved in tetrahydrofuran (55 ml), methanol (55 ml) and KH2PO4-Na2HPO4 buffer (pH 6.5, 70 ml), and 25% glutaraldehyde aqueous solution (1.22 g) and sodium cyanoborohydride (1.32 g) were added under ice-cooling. The mixture was stirred at room temperature for 17 days. Water (100 ml) was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous hydrogencarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was subjected to silica gel column chromatography to give the objective 2-(4-tert-butylphenyl)-5-(4-piperidinophenyl)-N-(2-thiazolyl)-imidazole-4-carboxamide (0.12 g), melting point 250-252° C. (decomposition).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous hydrogencarbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-57678c6144894d259342a6384d952d80
Source dataset
uspto-grants-2001_09
Patent number
US06288061B1

Reaction notes

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