HCID 118414938, compound → HCID 178469342, compound

HRID 1054309Notes

Reaction equation

HRID 1054309 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:10][CH:9]=2)[N:5]=[C:4]([CH3:21])[C:3]=1[C:22](O)([CH2:28][C:29]([O:31]CC)=O)[C:23]([O:25][CH2:26][CH3:27])=[O:24]>CC(O)=O>[OH:31][C:29]1[CH:28]=[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:3]2[C:4]([CH3:21])=[N:5][N:6]([CH2:7][C:8]3[CH:9]=[CH:10][C:11]([O:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[CH:12][CH:13]=3)[C:2]=2[N:1]=1

Participants

3

Reactant 1

HCID 118414938HCID 118414938, compound

Product 1

HCID 178469342HCID 178469342, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A suspension of diethyl 2-(5-amino-3-methyl-1-(4-phenoxybenzyl)-1H-pyrazol-4-yl)-2-hydroxysuccinate (crude from above) (2.31 mmol) from x in glacial AcOH (14 mL) was refluxed for 2 h. The mixture was concentrated under reduced pressure as much as possible. Then MeOH was added and the product crystallized as a white solid which was filtered, washed with cold MeOH and dried in a vacuum oven to provide the title compound (628 mg, 67% over two steps) as a tan solid. 1H NMR (500 MHz, CDCl3) δ 7.40 (d, J=8.3 Hz, 2H), 7.31 (t, J=7.3 Hz, 2H), 7.09 (t, J=7.4 Hz, 1H), 6.97 (d, J=8.0 Hz, 2H), 6.92 (d, J=8.4 Hz, 2H), 6.78 (s, 1H), 5.50 (s, 2H), 4.44 (q, J=7.1 Hz, 2H), 2.53 (s, 3H), 1.43 (t, J=7.1 Hz, 3H). 13C NMR (125 MHz, CDCl3) δ 164.83, 164.75, 157.17, 156.81, 143.45, 143.12, 139.06, 130.59, 129.72, 129.51, 123.43, 119.11, 118.70, 113.27, 103.16, 62.13, 50.60, 15.44, 14.16. ESI MS: m/z 404.1 (M+H)+.

Workup

  1. temperaturewas refluxed for 2 h
  2. concentrationThe mixture was concentrated under reduced pressure as much as possible
  3. additionThen MeOH was added
  4. customthe product crystallized as a white solid which
  5. filtrationwas filtered
  6. washwashed with cold MeOH
  7. customdried in a vacuum oven

Sources & evidence

ORD record
ord-a9f705a744f84eed9b2e7af64351173a
Source dataset
uspto-grants-2016_07
Patent number
US09394303B2

Reaction notes

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