Butyric Acid → HCID 86625844, compound

HRID 644142Notes

Reaction equation

HRID 644142 reaction equation
CN1CCCC1=O.[C:8]([OH:13])(=O)[CH2:9][CH2:10][CH3:11].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:26][C:27](=[N:57]O)[C:28]1[CH:56]=[CH:55][C:31]([O:32][CH2:33][CH2:34][CH2:35][CH:36]2[CH2:41][CH2:40][N:39]([CH2:42][CH2:43][CH2:44][O:45][C:46]3[CH:54]=[CH:53][C:49]([C:50]([NH2:52])=[O:51])=[CH:48][CH:47]=3)[CH2:38][CH2:37]2)=[CH:30][CH:29]=1>O.C(OCC)(=O)C>[NH2:57][C:27](=[N:26][O:13][CH2:8][CH2:9][CH2:10][CH3:11])[C:28]1[CH:56]=[CH:55][C:31]([O:32][CH2:33][CH2:34][CH2:35][CH:36]2[CH2:41][CH2:40][N:39]([CH2:42][CH2:43][CH2:44][O:45][C:46]3[CH:47]=[CH:48][C:49]([C:50]([NH2:52])=[O:51])=[CH:53][CH:54]=3)[CH2:38][CH2:37]2)=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 264Butyric AcidHCID 13387N-methyl-2-pyrrolidone2×HCID 682631,1'-CarbonyldiimidazoleHCID 86625843HCID 86625843, compound

Product 1

HCID 86625844HCID 86625844, compoundYield 97.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To an N-methyl-2-pyrrolidone (10 mL) solution of 0.42 g of butyric 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 at the same temperature for 14 hours. The reaction mixture was added to a mixture of ethyl acetate and water. The precipitate was collected by filtration and washed with ethyl acetate to provide 1.10 g of 4-{3-[4-(3-{4-[amino(n-butyloxyimino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}benzamide=O-(butyryl)oxime as white solid form.

Workup

  1. stirringwhich was then stirred at the same temperature for 14 hours
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-32613c10bbcf479bbe9f134aa7bf6381
Source dataset
uspto-grants-2010_04
Patent number
US07700623B2

Reaction notes

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