HCID 58677534, compound → HCID 58677522, compound

HRID 1012650Notes

Reaction equation

HRID 1012650 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:18]2[CH:23]=[C:22]([O:24][CH2:25][CH2:26][CH2:27][OH:28])[CH:21]=[CH:20][C:19]=2[CH3:29])=[O:17])=[C:12]([N+:30]([O-])=O)[CH:11]=1>CCO>[NH2:30][C:12]1[CH:11]=[C:10]([NH:9][C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])[CH:15]=[CH:14][C:13]=1[C:16]([C:18]1[CH:23]=[C:22]([O:24][CH2:25][CH2:26][CH2:27][OH:28])[CH:21]=[CH:20][C:19]=1[CH3:29])=[O:17]

Participants

3

Reactant 1

HCID 58677534HCID 58677534, compound

Product 1

HCID 58677522HCID 58677522, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound 307 (46 mg, 0.1 mmol) was dissolved in EtOH (5 mL), flushed with argon and added Pd/C (cat. amount). The flask was purged with H2 for 2 min. and stirred under an H2-atmosphere at RT for 1 h. The reaction mixture was filtered through Celite and concentrated in vacuo. Purified by continuously gradient flash chromatography using DCM/MeOH (v:v=100:0 to 95:5) as the eluent, affording the title compound as a yellow oil. 13C NMR (DMSO-d6) δ 196.3, 158.9 (dd), 156.2, 155.6 (dd), 154.2, 150.8, 142.2, 135.6, 131.1, 127.0 (dd), 125.2, 124.8 (dd), 114.5, 112.2, 111.6 (dd), 109.7, 104.8 (dd), 104.0, 96.9, 64.6, 57.2, 32.1, 17.9

Workup

  1. customflushed with argon
  2. additionadded Pd/C (cat. amount)
  3. customThe flask was purged with H2 for 2 min.
  4. filtrationThe reaction mixture was filtered through Celite
  5. concentrationconcentrated in vacuo
  6. customPurified by continuously gradient flash chromatography

Sources & evidence

ORD record
ord-2a54686ab6bf43e7acc22f9b06d98fa0
Source dataset
uspto-grants-2011_07
Patent number
US07977387B2

Reaction notes

Loading…