Ethyl 2-methylacetoacetate → HCID 178432046, compound

HRID 348018Notes

Reaction equation

HRID 348018 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[C:10]([NH2:13])[NH:11][N:12]=1.C([O:23][C:24](=O)[CH:25]([CH3:29])[C:26](=O)[CH3:27])C.C(OCC)C>C(O)(=O)C>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([C:9]2[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])=[N:12][N:11]3[C:24]([OH:23])=[C:25]([CH3:29])[C:26]([CH3:27])=[N:13][C:10]=23)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 701Ethyl 2-methylacetoacetateHCID 3283Diethyl EtherHCID 178509105HCID 178509105, compound

Product 1

HCID 178432046HCID 178432046, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 5-(2-chlorophenyl)-4-(4-chlorophenyl)-2H-pyrazol-3-ylamine (I-3A-1b; 0.642 g, 2.11 mmol) in acetic acid (2.6 ml) was added 2-methyl-3-oxobutyric acid ethyl ester (366 mg, 2.53 mmol). The reaction was heated at 100° C. for 5 hours. After cooling to room temperature, the precipitated solid was isolated by vacuum filtration and then repulped from diethyl ether to afford I-4A-1a (292 mg, 36%) as a colorless solid: +ESI MS (M+1) 384.1; 1H NMR (400 MHz, DMSO-d6) δ 11.77 (s, 1H), 7.45–7.33 (m, 6H), 7.11 (d, J=8.7 Hz, 2H), 2.33 (s, 3H), 1.99 (s, 3H).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe precipitated solid was isolated by vacuum filtration
  3. customto afford I-4A-1a (292 mg, 36%) as a colorless solid

Sources & evidence

ORD record
ord-833764f739c34cedb55d15ad90161150
Source dataset
uspto-grants-2007_02
Patent number
US07176210B2

Reaction notes

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