Potassium → N-cyclohexyl-N-methyl-7-(3H-imidazo[4,5-c]pyridin-3-yl)heptanamide

HRID 1088224Notes

Reaction equation

HRID 1088224 reaction equation
[N:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[N:3]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=O)[CH:2]=1.[N:19]1([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]C(O)=O)[C:27]2C=CN=CC=2N=C1.N1(CC2C=CC(C(O)=O)=CC=2)C2C=CN=CC=2N=C1.[K]>>[CH:28]1([N:19]([CH3:27])[C:16](=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][N:3]2[C:4]3[CH:5]=[N:6][CH:7]=[CH:8][C:9]=3[N:1]=[CH:2]2)[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]1

Participants

5

Reactant 4

HCID 5462222PotassiumHCID 143697714-(1H-imidazo[4,5-c]pyridin-1-ylmethyl)benzoic acidHCID 148360757-(3H-imidazo[4,5-c]pyridin-3-yl)heptanoic acidHCID 148360777-(1H-imidazo[4,5-c]pyridin-1-yl)heptanoic acid

Product 1

HCID 14369755N-cyclohexyl-N-methyl-7-(3H-imidazo[4,5-c]pyridin-3-yl)heptanamide

Procedure

Utilizing the procedure described in Example 5(b) employin a mixture of 7-(3H-imidazo[4,5-c]pyridin-3-yl)heptanoic acid and 7-(1H-imidazo[4,5-c]pyridin-1-yl)heptanoic acid, potassium salts in lieu of 4-(1H-imidazo[4,5-c]pyridin-1-ylmethyl) benzoic acid, potassium salt yielded an impure mixture of isomers. The mixture was purified by column chromatography (silica gel, 5% ethanol in chloroform) to yield a less polar isomer N-cyclohexyl-N-methyl-7-(3H-imidazo[4,5-c]pyridin-3-yl)heptanamide as a pale-yellow oil, having the following physical characteristics:

Workup

  1. customyielded
  2. additionan impure mixture of isomers
  3. customThe mixture was purified by column chromatography (silica gel, 5% ethanol in chloroform)

Sources & evidence

ORD record
ord-aabc6151fcdc4527998de489007fe6cb
Source dataset
uspto-grants-1990_10
Patent number
US04962106

Reaction notes

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