3-acetyl-1H-pyrazole-5-carboxylic acid → HCID 70656462, compound

HRID 872766Notes

Reaction equation

HRID 872766 reaction equation
[NH2:1][C@@H:2]([CH3:19])[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])[C:10]=2[F:18])=[N:5]1.[C:20]([C:23]1[CH:27]=[C:26]([C:28](O)=[O:29])[NH:25][N:24]=1)(=[O:22])[CH3:21]>CN(C=O)C>[C:20]([C:23]1[CH:27]=[C:26]([C:28]([NH:1][C@@H:2]([CH3:19])[CH2:3][N:4]2[CH:8]=[CH:7][C:6]([C:9]3[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([Cl:17])[C:10]=3[F:18])=[N:5]2)=[O:29])[NH:25][N:24]=1)(=[O:22])[CH3:21]

Participants

4

Reactant 2

HCID 167673463-acetyl-1H-pyrazole-5-carboxylic acidHCID 67172691HCID 67172691, compound

Product 1

HCID 70656462HCID 70656462, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was synthesized from (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-3-fluorobenzonitrile (0.05 g, 0.18 mmol) and 3-acetyl-1H-pyrazole-5-carboxylic acid (0.028 g, 0.18 mmol) using DMF (3 mL) as solvent using the method of Example 34(d). Yield 0.056 g. 1H NMR (400 MHz; CDCl3): δ 1.16 (d, 3H), 2.46 (s, 3H), 4.29 (m, 2H), 4.49 (m, 1H), 6.70 (dd, 1H), 7.17 (bs, 1H), 7.50 (m, 2H), 8.06 (m, 1H).

Sources & evidence

ORD record
ord-90eb92550a8248a5952c3b19f66f6f04
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

Loading…