2-Ethyl-4-Methyl-1H-Imidazole-5-Carbaldehyde → HCID 178437668, compound

HRID 493112Notes

Reaction equation

HRID 493112 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:25][C:14]3=[N:15][CH:16]=[CH:17][C:18]([N:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)=[C:13]3[N:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:26]([C:28]1[NH:29][C:30]([CH3:35])=[C:31]([CH:33]=O)[N:32]=1)[CH3:27].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN1C(=O)CCC1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:25][C:14]3=[N:15][CH:16]=[CH:17][C:18]([N:19]4[CH2:20][CH2:21][N:22]([CH2:35][C:30]5[N:29]=[C:28]([CH2:26][CH3:27])[NH:32][C:31]=5[CH3:33])[CH2:23][CH2:24]4)=[C:13]3[N:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 27958842-Ethyl-4-Methyl-1H-Imidazole-5-CarbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 178440762HCID 178440762, compound

Product 1

HCID 178437668HCID 178437668, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

2-(4-tert-Butyl-phenyl)-7-piperazin-1-yl imidazo[4,5-b]pyridine (7) (50 mg, 0.15 mmol) and 2-ethyl-5-methyl-1H-imidazole-4-carbaldehyde (21 mg, 0.15 mmol) were dissolved in NMP (4 ml) with sodium triacetoxyborohydride (64 mg, 0.30 mmol). The reaction mixture was allowed to stir for 18 hours under nitrogen. It was judged complete by MS, and purified by HPLC Method E to yield the title product 8 (23 mg (33%), 0.05 mmol). 1H NMR (DMSO-d6): δ 8.09 (d, J=8.3 Hz, 3H), 7.59 (d, J=8.3 Hz, 2H), 6.80 (s, 1H), 3.80-4.00 (m, 8H), 2.84 (q, J=7.7 Hz, 2H), 2.25 (s, 3H), 1.31 (m, 12H). The product 8 was determined to be 96% pure by analytical HPLC. MS (ESI-POS): [M+H]+=458; MS(ESI-NEG):[M−H]−=456.

Workup

  1. custompurified by HPLC Method E

Sources & evidence

ORD record
ord-69d3d289c70d4f3d95eb0155c4fecf03
Source dataset
uspto-grants-2009_05
Patent number
US07534796B2

Reaction notes

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