Ethanol → HCID 448379, compound

HRID 644799Notes

Reaction equation

HRID 644799 reaction equation
[CH3:1][N:2]([CH3:38])[CH2:3][CH2:4][CH2:5][NH:6][C:7]([C:9]1[N:10]=[C:11]([NH:17][C:18]([C:20]2[N:21]([CH3:37])[CH:22]=[C:23]([NH:25][C:26]([C:28]3[N:29]([CH3:36])[CH:30]=[C:31]([N+:33]([O-])=O)[CH:32]=3)=[O:27])[CH:24]=2)=[O:19])[S:12][C:13]=1[CH:14]([CH3:16])[CH3:15])=[O:8].[CH2:39]([OH:41])C>[Pd]>[CH3:1][N:2]([CH3:38])[CH2:3][CH2:4][CH2:5][NH:6][C:7]([C:9]1[N:10]=[C:11]([NH:17][C:18]([C:20]2[N:21]([CH3:37])[CH:22]=[C:23]([NH:25][C:26]([C:28]3[N:29]([CH3:36])[CH:30]=[C:31]([NH:33][CH:39]=[O:41])[CH:32]=3)=[O:27])[CH:24]=2)=[O:19])[S:12][C:13]=1[CH:14]([CH3:16])[CH3:15])=[O:8]

Participants

4

Reactant 2

HCID 702EthanolHCID 11249756HCID 11249756, compound

Product 1

HCID 448379HCID 448379, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

N-[3-(Dimethylamino)propyl]-5-isopropyl-2-{[(1-methyl-4-{[(1-methyl-4-nitro-1H-pyrrol-2-yl)carbonyl]amino}-1H-pyrrol-2-yl)carbonyl]amino}-1,3-thiazole-4-carboxamide (90 mg, 0.165 mmol; see step (v) above) was suspended in ethanol (20 mL) then Pd/C (97 mg, 10%) was added at 0° C. under nitrogen. The reaction mixture was hydrogenated at room temperature and atmospheric pressure for 5 h. The catalyst was removed under reduced pressure then ethyl formate (20 mL) was added to the ethanolic solution of the amine. The reaction mixture was heated under reflux for 3 days, then the solvent was removed under reduced pressure. The crude product was dissolved in water (2 mL) containing 0.1% TFA, then purified by HPLC. The fractions collected were freeze-dried to give the desired product as pale yellow solid (55 mg, 51%) with no distinct m.p.

Workup

  1. customwas hydrogenated at room temperature
  2. customThe catalyst was removed under reduced pressure
  3. additionethyl formate (20 mL) was added to the ethanolic solution of the amine
  4. temperatureThe reaction mixture was heated
  5. temperatureunder reflux for 3 days
  6. customthe solvent was removed under reduced pressure
  7. dissolutionThe crude product was dissolved in water (2 mL)
  8. additioncontaining 0.1% TFA
  9. custompurified by HPLC
  10. customThe fractions collected
  11. customwere freeze-dried

Sources & evidence

ORD record
ord-8a523a9f69754a3e802dd74e6d53eb7c
Source dataset
uspto-grants-2010_04
Patent number
US07700765B2

Reaction notes

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