Pivalic acid → HCID 86625845, compound

HRID 644143Notes

Reaction equation

HRID 644143 reaction equation
CN1CCCC1=O.[C:8]([OH:14])(=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:27][C:28](=[N:58]O)[C:29]1[CH:57]=[CH:56][C:32]([O:33][CH2:34][CH2:35][CH2:36][CH:37]2[CH2:42][CH2:41][N:40]([CH2:43][CH2:44][CH2:45][O:46][C:47]3[CH:55]=[CH:54][C:50]([C:51]([NH2:53])=[O:52])=[CH:49][CH:48]=3)[CH2:39][CH2:38]2)=[CH:31][CH:30]=1>O.C(OCC)(=O)C>[NH2:58][C:28](=[N:27][O:13][C:8](=[O:14])[C:9]([CH3:12])([CH3:11])[CH3:10])[C:29]1[CH:57]=[CH:56][C:32]([O:33][CH2:34][CH2:35][CH2:36][CH:37]2[CH2:42][CH2:41][N:40]([CH2:43][CH2:44][CH2:45][O:46][C:47]3[CH:48]=[CH:49][C:50]([C:51]([NH2:53])=[O:52])=[CH:54][CH:55]=3)[CH2:39][CH2:38]2)=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 6417Pivalic acidHCID 13387N-methyl-2-pyrrolidone2×HCID 682631,1'-CarbonyldiimidazoleHCID 86625843HCID 86625843, compound

Product 1

HCID 86625845HCID 86625845, compoundYield 68.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To an N-methyl-2-pyrrolidone (10 mL) solution of 0.47 g of pivalic acid was added 0.76 g of 1,1′-carbonyldiimidazole at room temperature, which was then stirred at the same temperature for 1 hour and 20 minutes. 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 2 hours. The reaction mixture was added a mixture of ethyl acetate and water. The precipitate was collected by filtration and washed with ethyl acetate to provide 0.81 g of 4-{3-[4-(3-{4-[amino(2,2-dimethylpropionyloxyimino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}benzamide=O-(2,2-dimethylpropionyl)oxime as white solid form.

Workup

  1. stirringwhich was then stirred at the same temperature for 2 hours
  2. additionThe reaction mixture was added
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-afeb7208f83546d595505d41604790ff
Source dataset
uspto-grants-2010_04
Patent number
US07700623B2

Reaction notes

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