HCID 68681124, compound → HCID 59464039, compound

HRID 1713760Notes

Reaction equation

HRID 1713760 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[O:14][C:13]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][CH:27](C(O)=O)[C:28]([OH:30])=[O:29])=[CH:20][CH:19]=3)=[O:16])=[N:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8]>CC(O)=O>[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[O:14][C:13]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[CH:20][CH:19]=3)=[O:16])=[N:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

3

Reactant 1

HCID 68681124HCID 68681124, compound

Product 1

HCID 59464039HCID 59464039, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of (3-{4-[({5-[(3,4-difluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]phenyl}propyl)malonic acid (Example 506) (40 mg, 0.087 mmol) in AcOH (4 mL) was heated under reflux with stirring for 4 h. The reaction mixture was concentrated in vacuo and the solid filtered and washed with water then Et2O to give the title compound (20 mg, 55%) as a solid; 1H NMR δ 1.50-1.60 (4H, m), 2.24 (2H, t), 2.55 (2H, t), 7.15-7.20 (2H, m), 7.35-7.37 (1H, m), 7.48-7.52 (1H, m), 7.68-7.73 (3H, m), 10.97 (1H, s); MS m/e MH+ 417.

Workup

  1. temperatureunder reflux
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. filtrationthe solid filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-e476f485b6e94bd4bcb93ec54d4015d7
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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