Acetic Acid → HCID 67435387, compound

HRID 1663392Notes

Reaction equation

HRID 1663392 reaction equation
[Br:1][C:2]1[C:3]([NH:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[N+:40]([O-])=O)=[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]=1.C(O)(=O)C>C1COCC1.[Zn]>[NH2:40][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=1[CH2:33][NH:32][C:3]1[C:2]([Br: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]=1[NH:25][S:26]([CH2:29][CH2:30][CH3:31])(=[O:27])=[O:28]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 67435394HCID 67435394, compound

Product 1

HCID 67435387HCID 67435387, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Propane-1-sulfonic acid [3-bromo-5-(3-cyano-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinolin-4-yl)-2-(2-nitro-benzylamino)-phenyl]-amide (1.21 g) and acetic acid (1.6 ml) were dissolved in THF (150 ml). Zinc dust (2.32 g) was added under vigorous stirring. After 3 h, the mixture was filtered, diluted with ethyl acetate and washed with sat. aq. NaHCO3. The residue was purified by chromatography on silicagel in heptane/ethyl acetate 1/0→0/1 (v/v) as eluent.

Workup

  1. filtrationthe mixture was filtered
  2. additiondiluted with ethyl acetate
  3. washwashed with sat. aq. NaHCO3
  4. customThe residue was purified by chromatography on silicagel in heptane/ethyl acetate 1/0→0/1 (v/v) as eluent

Sources & evidence

ORD record
ord-04c92ddf3ab64b668b68d170e695a74c
Source dataset
uspto-grants-2011_10
Patent number
US08034945B2

Reaction notes

Loading…