Thionyl Chloride → Ethyl cis(+/-)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-1,3-oxazole-4-carboxylate

HRID 43604Notes

Reaction equation

HRID 43604 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:9]([OH:11])=O)[NH:5][C:6]=1[CH2:7][CH3:8].S(Cl)(Cl)=O.[NH2:16][C@H:17]1[CH2:22][CH2:21][N:20]([C:23]2[O:24][CH:25]=[C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:27]=2)[CH2:19][C@H:18]1[O:33][CH3:34]>>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:16][C@H:17]2[CH2:22][CH2:21][N:20]([C:23]3[O:24][CH:25]=[C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:27]=3)[CH2:19][C@H:18]2[O:33][CH3:34])=[O:11])[NH:5][C:6]=1[CH2:7][CH3:8]

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 675489294-chloro-5-ethyl-1H-imidazole-2-carboxylic acidHCID 86648577Ethyl cis(+/-)-2-(4-amino-3-methoxypiperidin-1-yl)-1,3-oxazole-4-carboxylate

Product 1

HCID 86648579Ethyl cis(+/-)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-1,3-oxazole-4-carboxylateYield 59.5%

Procedure

The same operation as in Example (91c) was performed using 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid (0.13 g, 0.75 mmol), thionyl chloride (2 mL) and ethyl cis(±)-2-(4-amino-3-methoxypiperidin-1-yl)-1,3-oxazole-4-carboxylate obtained in Example (103d) (0.3 g, 1.12 mmol). Purification by silica gel column chromatography (elution solvent: ethyl acetate/hexane=4/1, 1/0) gave 0.19 g of the title compound as a brown oily substance (60%).

Workup

  1. customPurification
  2. washby silica gel column chromatography (elution solvent: ethyl acetate/hexane=4/1, 1/0)

Sources & evidence

ORD record
ord-455df27106854f048040999cd490f210
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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