1H-Imidazole-4-carbaldehyde → HCID 67498423, compound

HRID 1628197Notes

Reaction equation

HRID 1628197 reaction equation
[NH2:1][C@@H:2]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:3]([NH:5][C:6]1[S:7][C:8]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[N:9][N:10]=1)=[O:4].[NH:24]1[CH:28]=[C:27]([CH:29]=O)[N:26]=[CH:25]1.[BH3-][C:32]#N.[Na+]>CO>[CH3:32][N:24]1[CH:28]=[C:27]([CH2:29][NH:1][C@@H:2]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:3]([NH:5][C:6]2[S:7][C:8]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)=[N:9][N:10]=2)=[O:4])[N:26]=[CH:25]1

Participants

5

Reactant 3

HCID 764281H-Imidazole-4-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 67497136HCID 67497136, compound

Product 1

HCID 67498423HCID 67498423, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (S)-2-amino-3-phenyl-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)propanamide (0.066 g, 0.20 mmol), 1H-imidazole-4-carbaldehyde (0.019 g, 0.20 mmol) in MeOH (2 mL) was heated to 55° C. for 15 min before addition of NaCNBH3 (0.038 g, 0.61 mmol) and let stir for 4 h. The crude mixture was then purified by RPHPLC to afford (S)-2-((1-methyl-1H-imidazol-4-yl)methylamino)-3-phenyl-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)propanamide (47.0 mg, 55%).

Workup

  1. customThe crude mixture was then purified by RPHPLC

Sources & evidence

ORD record
ord-1730b13016784c35a60bd4563c2513b2
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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