Hydrochloric Acid → HCID 22609594, compound

HRID 2306781Notes

Reaction equation

HRID 2306781 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:13]=[CH:14]/[CH:15]=[CH:16]/[C:17]([N:19]2[CH2:24][CH2:23][N:22]([C:25](=[O:42])/[CH:26]=[CH:27]/[CH:28]=[CH:29]/[C:30]3[CH:35]=[C:34]([O:36][CH3:37])[C:33]([O:38][CH3:39])=[C:32]([O:40][CH3:41])[CH:31]=3)[CH2:21][CH:20]2[C:43]([OH:45])=O)=[O:18])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH3:59][NH:60][OH:61].C(N(CC)CC)C.Cl>CN(C)C=O>[CH3:12][O:11][C:7]1[CH:6]=[C:5](/[CH:13]=[CH:14]/[CH:15]=[CH:16]/[C:17]([N:19]2[CH2:24][CH2:23][N:22]([C:25](=[O:42])/[CH:26]=[CH:27]/[CH:28]=[CH:29]/[C:30]3[CH:31]=[C:32]([O:40][CH3:41])[C:33]([O:38][CH3:39])=[C:34]([O:36][CH3:37])[CH:35]=3)[CH2:21][CH:20]2[C:43]([N:60]([CH3:59])[OH:61])=[O:45])=[O:18])[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 77906N-methylhydroxylamine hydrochlorideHCID 22609489HCID 22609489, compound

Product 1

HCID 22609594HCID 22609594, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Added to a solution of 148 mg (0.24 mmol) of 1,4-bis[5-(3,4,5-trimethoxyphenyl)penta-(2E,4E)-dienoyl]-piperazine-2-carboxylic acid synthesized by the process of Example 34 in anhydrous dimethylformamide (0.5 ml) was 44.9 mg (0.28 mmol) of 1,1′-carbonyldiimidazole. After the mixture was stirred for 15 minutes, 24.9 mg (0.30 mmol) of N-methylhydroxyamine hydrochloride and 0.050 ml (0.36 mmol) of triethylamine were added, and the mixture was stirred for an additional 15 minutes. Added to the reaction mixture was 3 ml of 0.5N hydrochloric acid to conduct extraction with chloroform. An organic layer was dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resultant crude oil (179 mg) was purified by column chromatography on silica gel to obtain 134.6 mg (yield: 87%) of the title compound as pale yellow amorphous powder.

Workup

  1. stirringthe mixture was stirred for an additional 15 minutes
  2. additionAdded to the reaction mixture
  3. extractionextraction with chloroform
  4. dry with materialAn organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resultant crude oil (179 mg) was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-431ebaac44e84fa8aa8152db40d77786
Source dataset
uspto-grants-2004_12
Patent number
US06828316B2

Reaction notes

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