Propionic Acid → HCID 86625842, compound

HRID 644141Notes

Reaction equation

HRID 644141 reaction equation
CN1CCCC1=O.[C:8]([OH:12])(=[O:11])[CH2:9][CH3:10].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:25][C:26](=[N:56]O)[C:27]1[CH:55]=[CH:54][C:30]([O:31][CH2:32][CH2:33][CH2:34][CH:35]2[CH2:40][CH2:39][N:38]([CH2:41][CH2:42][CH2:43][O:44][C:45]3[CH:53]=[CH:52][C:48]([C:49]([NH2:51])=[O:50])=[CH:47][CH:46]=3)[CH2:37][CH2:36]2)=[CH:29][CH:28]=1>O.C(Cl)(Cl)Cl>[NH2:56][C:26](=[N:25][O:11][C:8](=[O:12])[CH2:9][CH3:10])[C:27]1[CH:55]=[CH:54][C:30]([O:31][CH2:32][CH2:33][CH2:34][CH:35]2[CH2:40][CH2:39][N:38]([CH2:41][CH2:42][CH2:43][O:44][C:45]3[CH:46]=[CH:47][C:48]([C:49]([NH2:51])=[O:50])=[CH:52][CH:53]=3)[CH2:37][CH2:36]2)=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 1032Propionic AcidHCID 13387N-methyl-2-pyrrolidone2×HCID 682631,1'-CarbonyldiimidazoleHCID 86625843HCID 86625843, compound

Product 1

HCID 86625842HCID 86625842, compoundYield 51.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To an N-methyl-2-pyrrolidone (10 mL) solution of 0.35 g of propionic acid was added 0.76 g of 1,1′-carbonyldiimidazole at room temperature, which was then stirred at the same temperature for one hour. An N-methyl-2-pyrrolidone (10 mL) solution of 1.00 g of 4-{3-[4-(3-{4-[amino(hydroxyimino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}benzamide=oxime was added to the mixture at room temperature, which was then stirred for 15 hours. The reaction mixture was added to a mixture of chloroform and water. The precipitate was collected by filtration and washed with ethyl acetate to provide 0.58 g of 4-{3-[4-(3-{4-[amino(propionyloxyimino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}benzamide=O-(propionyl)oxime as white solid form.

Workup

  1. stirringwhich was then stirred for 15 hours
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-8dd0d288787147b7ad9784038b002415
Source dataset
uspto-grants-2010_04
Patent number
US07700623B2

Reaction notes

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