Triethylamine → HCID 67435007, compound

HRID 1663388Notes

Reaction equation

HRID 1663388 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:20]2[C:29]3[C:28](=[O:30])[CH2:27][CH:26]([CH2:31][CH2:32][CH3:33])[CH2:25][C:24]=3[NH:23][C:22]([CH3:34])=[C:21]2[C:35]#[N:36])[CH:5]=[C:6]([Br:19])[C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=1.C(N(CC)CC)C.[CH3:44][S:45](Cl)(=[O:47])=[O:46]>ClCCl.C(OCC)(=O)C>[Br:19][C:6]1[C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=2)=[C:2]([NH:1][S:45]([CH3:44])(=[O:47])=[O:46])[CH:3]=[C:4]([CH:20]2[C:29]3[C:28](=[O:30])[CH2:27][CH:26]([CH2:31][CH2:32][CH3:33])[CH2:25][C:24]=3[NH:23][C:22]([CH3:34])=[C:21]2[C:35]#[N:36])[CH:5]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67434807HCID 67434807, compound

Product 1

HCID 67435007HCID 67435007, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-[3-amino-5-bromo-4-(3-nitro-benzyloxy)-phenyl]-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile (1.15 g) and triethylamine (740 μl) in dichloromethane (20 ml) was treated with methanesulfonyl chloride (203 μl). After stirring for 18 h, the mixture was diluted with ethyl acetate and washed with water. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The crude N,N-bis-methanesulfonyl-aniline derivative was dissolved in THF (20 ml) and treated with 2N NaOH (3 ml). After 2 h, the mixture was quenched with sat. aq. NH4Cl and extracted with ethyl acetate. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by chromatography on silicagel in heptane/ethyl acetate 1/0→0/1 (v/v) as eluent.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe crude N,N-bis-methanesulfonyl-aniline derivative was dissolved in THF (20 ml)
  6. additiontreated with 2N NaOH (3 ml)
  7. waitAfter 2 h
  8. customthe mixture was quenched with sat. aq. NH4Cl
  9. extractionextracted with ethyl acetate
  10. dry with materialThe organic layer was dried (MgSO4)
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. 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-77c0daf726dc4f829e6649916e848e24
Source dataset
uspto-grants-2011_10
Patent number
US08034945B2

Reaction notes

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