Acetic Acid → HCID 67434330, compound

HRID 1663393Notes

Reaction equation

HRID 1663393 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]2[C:17]3[C:16](=[O:18])[CH2:15][CH:14]([CH2:19][CH2:20][CH3:21])[CH2:13][C:12]=3[NH:11][C:10]([CH3:22])=[C:9]2[C:23]#[N:24])[CH:5]=[C:4]([NH:25][S:26]([CH2:29][CH2:30][CH3:31])(=[O:28])=[O:27])[C:3]=1[NH:32][C:33](=[O:43])[C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([N+:40]([O-])=O)[CH:35]=1.C(O)(=O)C>C1COCC1.[Zn]>[NH2:40][C:36]1[CH:35]=[C:34]([CH:39]=[CH:38][CH:37]=1)[C:33]([NH:32][C:3]1[C:4]([NH:25][S:26]([CH2:29][CH2:30][CH3:31])(=[O:28])=[O:27])=[CH:5][C:6]([CH:8]2[C:17]3[C:16](=[O:18])[CH2:15][CH:14]([CH2:19][CH2:20][CH3:21])[CH2:13][C:12]=3[NH:11][C:10]([CH3:22])=[C:9]2[C:23]#[N:24])=[CH:7][C:2]=1[Br:1])=[O:43]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 67435717HCID 67435717, compound

Product 1

HCID 67434330HCID 67434330, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[2-bromo-4-(3-cyano-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinolin-4-yl)-6-(propane-1-sulfonylamino)-phenyl]-3-nitro-benzamide (412 mg) and acetic acid (520 μl) in THF (10 ml), cooled to 0° C., was added zinc dust (810 mg) under vigorous stirring. After stirring for 4 h, the mixture was filtered and concentrated in vacuo. The residue was dissolved in dichloromethane and washed with water. The organic layer was dried (MgSO4), filtered and concentrated in vacuo.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed with water
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-98b63aba063a4039ab23503fb0a3f885
Source dataset
uspto-grants-2011_10
Patent number
US08034945B2

Reaction notes

Loading…