HCID 58677597, compound → HCID 58677619, compound

HRID 1012646Notes

Reaction equation

HRID 1012646 reaction equation
[OH:1][CH:2]([CH2:32][OH:33])[CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH3:31])=[C:9]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=3[CH3:27])=[CH:15][C:14]=2[N+:28]([O-])=O)=[O:12])[CH:10]=1>CO.[Pd]>[NH2:28][C:14]1[CH:15]=[C:16]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=2[CH3:27])[CH:17]=[CH:18][C:13]=1[C:11]([C:9]1[CH:10]=[C:5]([O:4][CH2:3][CH:2]([OH:1])[CH2:32][OH:33])[CH:6]=[CH:7][C:8]=1[CH3:31])=[O:12]

Participants

4

Reactant 1

HCID 58677597HCID 58677597, compound

Product 1

HCID 58677619HCID 58677619, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Compound 302 (0.025 g, 0.055 mmol) was dissolved in MeOH (2 mL). A catalytic amount of palladium on charcoal was added and the mixture was stirred under a hydrogen atmosphere for 1 h. The suspension was filtered and the filtrate was concentrated in vacuo. The crude product was purified by preparative HPLC. This afforded the title compound. 1H NMR (CDCl3) δ 7.19 (dd, 1H), 7.13 (d, 1H), 7.05-6.82 (m, 4H), 6.76 (d, 1H), 6.46 (bs, 2H), 5.89 (dd, 1H), 5.75 (d, 1H), 5.56 (bs, 1H), 4.15-3.93 (m, 3H), 3.80 (dd, 1H), 3.71 (dd, 1H), 2.65 (bs, 1H), 2.23 (s, 3H), 2.19 (s, 3H), 2.10 (bs, 1H)

Workup

  1. filtrationThe suspension was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-d055eb2d1b3b420eaa8768eb0fdf0c56
Source dataset
uspto-grants-2011_07
Patent number
US07977387B2

Reaction notes

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