Isobutyryl chloride → N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-2-methylpropanamide

HRID 11364Notes

Reaction equation

HRID 11364 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[C:13]2[C:12]([CH3:14])=[C:11]([CH3:15])[N:10]=[C:9]([NH2:16])[C:8]=2[N:7]=[C:6]1[CH2:17][O:18][CH2:19][CH3:20].[C:21](Cl)(=[O:25])[CH:22]([CH3:24])[CH3:23]>>[NH2:16][C:9]1[C:8]2[N:7]=[C:6]([CH2:17][O:18][CH2:19][CH3:20])[N:5]([CH2:4][CH2:3][CH2:2][NH:1][C:21](=[O:25])[CH:22]([CH3:24])[CH3:23])[C:13]=2[C:12]([CH3:14])=[C:11]([CH3:15])[N:10]=1

Participants

3

Reactant 2

HCID 62325Isobutyryl chlorideHCID 219738361-(3-aminopropyl)-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine

Product 1

HCID 10150053N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-2-methylpropanamideYield 59.2%

Procedure

Using the method of Example 19, 1-(3-aminopropyl)-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine (1.00 g, 3.6 mmol) was reacted with isobutyryl chloride (0.42 mL, 40 mmol) to provide 0.74 g of N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-2-methylpropanamide as an off white solid, m.p. 179.1–179.7° C.

Sources & evidence

ORD record
ord-cdbf41f59d6d4d6e829fa4e5b4ee6fc3
Source dataset
uspto-grants-2006_08
Patent number
US07098221B2

Reaction notes

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