Pyridine → HCID 67435761, compound

HRID 1663390Notes

Reaction equation

HRID 1663390 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:36]=[CH:37][CH:38]=1)[CH2:5][O:6][C:7]1[C:12]([Br:13])=[CH:11][C:10]([CH:14]2[C:23]3[C:22](=[O:24])[CH2:21][CH:20]([CH2:25][CH2:26][CH3:27])[CH2:19][C:18]=3[NH:17][C:16]([CH3:28])=[C:15]2[C:29]#[N:30])=[CH:9][C:8]=1[NH:31][S:32]([CH3:35])(=[O:34])=[O:33].N1C=CC=CC=1.[CH3:45][S:46](Cl)(=[O:48])=[O:47]>ClCCl.C(OCC)(=O)C>[Br:13][C:12]1[C:7]([O:6][CH2:5][C:4]2[CH:36]=[CH:37][CH:38]=[C:2]([NH:1][S:46]([CH3:45])(=[O:48])=[O:47])[CH:3]=2)=[C:8]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])[CH:9]=[C:10]([CH:14]2[C:23]3[C:22](=[O:24])[CH2:21][CH:20]([CH2:25][CH2:26][CH3:27])[CH2:19][C:18]=3[NH:17][C:16]([CH3:28])=[C:15]2[C:29]#[N:30])[CH:11]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 67434762HCID 67434762, compound

Product 1

HCID 67435761HCID 67435761, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-[2-(3-amino-benzyloxy)-3-bromo-5-(3-cyano-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinolin-4-yl)-phenyl]-methanesulfonamide (709 mg) and pyridine (286 μl) in dichloromethane (20 ml) was added methanesulfonyl chloride (138 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 residue was purified by preparative HPLC (Method B).

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative HPLC (Method B)

Sources & evidence

ORD record
ord-975351b3708a465f85865e1f52495118
Source dataset
uspto-grants-2011_10
Patent number
US08034945B2

Reaction notes

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