3-acetyl-1H-pyrazole-5-carboxylic acid → HCID 70656455, compound

HRID 872596Notes

Reaction equation

HRID 872596 reaction equation
[NH2:1][C@H:2]([CH3:20])[CH2:3][N:4]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([N+:17]([O-:19])=[O:18])[C:12]([C:15]#[N:16])=[N:13][CH:14]=2)=[N:5]1.[C:21]([C:24]1[CH:28]=[C:27]([C:29](O)=[O:30])[NH:26][N:25]=1)(=[O:23])[CH3:22]>>[C:21]([C:24]1[CH:28]=[C:27]([C:29]([NH:1][C@H:2]([CH3:20])[CH2:3][N:4]2[CH:8]=[CH:7][C:6]([C:9]3[CH:14]=[N:13][C:12]([C:15]#[N:16])=[C:11]([N+:17]([O-:19])=[O:18])[CH:10]=3)=[N:5]2)=[O:30])[NH:26][N:25]=1)(=[O:23])[CH3:22]

Participants

3

Reactant 2

HCID 167673463-acetyl-1H-pyrazole-5-carboxylic acidHCID 70656800HCID 70656800, compound

Product 1

HCID 70656455HCID 70656455, compoundYield 19%

Procedure

(R)-5-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-3-nitropicolinonitrile (0.62 g, 1.14 mmol) was coupled with 3-acetyl-1H-pyrazole-5-carboxylic acid (0.39 g, 2.50 mmol) using the method of Example 34(d). Crude product was purified twice by CombiFlash (1st column: silica, eluent: 0-10% MeOH in DCM; 2nd column: C-18, eluent: 0-100% MeCN in water) to yield 86 mg (19%) of the title compound. 1H-NMR (400 MHz; CDCl3): δ 1.23 (d, 3H), 2.56 (s, 3H), 4.33 (dd, 1H), 4.55 (dd, 1H), 4.58-4.67 (m, 1H), 6.83-6.86 (m, 1H), 7.29-7.31 (broad s, 1H), 7.65 (d, 1H), 8.91-8.94 (broad s, 1H), 9.64-9.67 (m, 1H).

Workup

  1. customCrude product was purified twice by CombiFlash (1st column: silica, eluent: 0-10% MeOH in DCM; 2nd column: C-18, eluent: 0-100% MeCN in water)

Sources & evidence

ORD record
ord-92555545959748709422fc095b748b72
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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