1-Propanesulfonyl chloride → HCID 67215851, compound

HRID 472928Notes

Reaction equation

HRID 472928 reaction equation
[CH2:1]([S:4](Cl)(=[O:6])=[O:5])[CH2:2][CH3:3].[NH2:8][C:9]1[CH:35]=[CH:34][C:12]([C:13]([C:15]2[N:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]3=[C:17]([C:24]3[CH:25]=[C:26]([CH:31]=[CH:32][CH:33]=3)[C:27]([O:29][CH3:30])=[O:28])[N:16]=2)=[O:14])=[CH:11][C:10]=1[O:36][CH3:37]>N1C=CC=CC=1.ClCCl>[CH3:37][O:36][C:10]1[CH:11]=[C:12]([CH:34]=[CH:35][C:9]=1[NH:8][S:4]([CH2:1][CH2:2][CH3:3])(=[O:6])=[O:5])[C:13]([C:15]1[N:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]2=[C:17]([C:24]2[CH:25]=[C:26]([CH:31]=[CH:32][CH:33]=2)[C:27]([O:29][CH3:30])=[O:28])[N:16]=1)=[O:14]

Participants

5

Reactant 2

HCID 662791-Propanesulfonyl chlorideHCID 67215653HCID 67215653, compound

Product 1

HCID 67215851HCID 67215851, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

0.17 ml (1.5 mmol) of 1-propanesulfonyl chloride is added to 0.5 g (1.24 mmol) of methyl 3-[3-(4-amino-3-methoxybenzoyl)imidazo[1,5-a]pyridin-1-yl]benzoate obtained in example 111 in 6 ml of pyridine. The reaction medium is stirred at ambient temperature for 18 h and then concentrated under reduced pressure. The residue obtained is taken up in dichloromethane. The organic phase obtained is washed with water, dried over sodium sulfate and concentrated under reduced pressure. The residue obtained is purified by column chromatography on silica gel, elution being carried out with dichloromethane. 0.34 g of a yellow oil is collected. MS+: 508; 1H NMR (d6-DMSO): 0.96-1.01 (3H, t), 1.74-1.81 (2H, m), 3.16-3.19 (2H, m), 3.92 (3H, s), 4.00 (3H, s), 7.33-7.73 (2H, m), 7.38-7.51 (1H, m), 7.53-7.96 (2H, m), 8.03-8.30 (2H, m), 8.33-9.85 (2H, m), 8.38 (1H, s), 8.63 (1H, s), 9.25 (1H, m)

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue obtained
  3. customThe organic phase obtained
  4. washis washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained
  8. customis purified by column chromatography on silica gel, elution
  9. custom0.34 g of a yellow oil is collected

Sources & evidence

ORD record
ord-2e68fea81faa44cbb76407261f0bb040
Source dataset
uspto-grants-2014_01
Patent number
US08633216B2

Reaction notes

Loading…