1-(6-methyl-2-pyridinyl)-1H-imidazole-4-carboxylic acid → HCID 70656033, compound

HRID 872902Notes

Reaction equation

HRID 872902 reaction equation
[NH2:1][C@@H:2]([CH3:18])[CH2:3][N:4]1[CH:8]=[CH:7][C:6]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([Cl:17])[CH:10]=2)=[N:5]1.[CH3:19][C:20]1[N:25]=[C:24]([N:26]2[CH:30]=[C:29]([C:31](O)=[O:32])[N:28]=[CH:27]2)[CH:23]=[CH:22][CH:21]=1>>[Cl:17][C:11]1[CH:10]=[C:9]([C:6]2[CH:7]=[CH:8][N:4]([CH2:3][C@@H:2]([NH:1][C:31]([C:29]3[N:28]=[CH:27][N:26]([C:24]4[CH:23]=[CH:22][CH:21]=[C:20]([CH3:19])[N:25]=4)[CH:30]=3)=[O:32])[CH3:18])[N:5]=2)[CH:16]=[CH:15][C:12]=1[C:13]#[N:14]

Participants

3

Reactant 2

HCID 14800051-(6-methyl-2-pyridinyl)-1H-imidazole-4-carboxylic acidHCID 67170882(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile

Product 1

HCID 70656033HCID 70656033, compound

Procedure

The title compound was prepared using the method of Example 34(d) starting from (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (220 mg, 0.844 mmol) and 1-(6-methylpyridin-2-yl)-1H-imidazole-4-carboxylic acid (223 mg, 1.097 mmol). The product was triturated with acetonitrile. Yield 153 mg (40%). 1H-NMR (400 MHz; CDCl3): δ 1.26 (d, 3H), 1.45 (s, 3H), 2.59 (s, 1H), 4.28-4.45 (m, 2H), 4.55-4.64 (m, 1H), 6.62 (d, 1H), 7.16 (d, 1H), 7.19 (d, 1H), 7.52 (d, 1H), 7.67 (d, 1H), 7.75 (t, 1H), 7.80 (m, 1H), 7.89 (d, 1H), 8.12 (d, 1H), 8.21 (d, 1H).

Workup

  1. customThe product was triturated with acetonitrile

Sources & evidence

ORD record
ord-b791df7370f44708b525edb8cc28db96
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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