Pyridine → HCID 67435104, compound

HRID 1663371Notes

Reaction equation

HRID 1663371 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:21]2[C:30]3[C:29](=[O:31])[CH2:28][CH:27]([CH2:32][CH2:33][CH3:34])[CH2:26][C:25]=3[NH:24][C:23]([CH3:35])=[C:22]2[C:36]#[N:37])[CH:5]=[C:6]([O:18][CH2:19][CH3:20])[C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=1.N1C=CC=CC=1.[CH2:44]([S:47](Cl)(=[O:49])=[O:48])[CH2:45][CH3:46]>ClCCl>[C:36]([C:22]1[CH:21]([C:4]2[CH:5]=[C:6]([O:18][CH2:19][CH3:20])[C:7]([O:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=3)=[C:2]([NH:1][S:47]([CH2:44][CH2:45][CH3:46])(=[O:49])=[O:48])[CH:3]=2)[C:30]2[C:29](=[O:31])[CH2:28][CH:27]([CH2:32][CH2:33][CH3:34])[CH2:26][C:25]=2[NH:24][C:23]=1[CH3:35])#[N:37]

Participants

5

Reactant 3

HCID 1049PyridineHCID 662791-Propanesulfonyl chlorideHCID 67435247HCID 67435247, compound

Product 1

HCID 67435104HCID 67435104, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-[3-amino-5-ethoxy-4-(3-methoxy-benzyloxy)-phenyl]-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile (220 mg) and pyridine (106 μl) in dichloromethane (5 ml) was added propane-1-sulfonyl chloride (94 mg). After stirring for 17 h, the mixture was diluted with dichloromethane and extracted with water and sat. aq. NaHCO3. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by preparative HPLC (Method B).

Workup

  1. extractionextracted with water and sat. aq. NaHCO3
  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-5dfd583ae2354d039552ac00226fee6e
Source dataset
uspto-grants-2011_10
Patent number
US08034945B2

Reaction notes

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