Diphenylacetic Acid → HCID 14403640, compound

HRID 1194148Notes

Reaction equation

HRID 1194148 reaction equation
O.OC1C2N=NNC=2C=CC=1.[C:12]1([CH:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19]([OH:21])=O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH3:28][O:29][C:30]([CH:32]1[NH:37][CH2:36][C:35]2[N:38]=[CH:39][N:40]([CH2:41][C:42]3[CH:47]=[CH:46][C:45]([N+:48]([O-:50])=[O:49])=[C:44]([CH3:51])[CH:43]=3)[C:34]=2[CH2:33]1)=[O:31]>C(#N)C>[CH3:28][O:29][C:30]([CH:32]1[N:37]([C:19](=[O:21])[CH:18]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:36][C:35]2[N:38]=[CH:39][N:40]([CH2:41][C:42]3[CH:47]=[CH:46][C:45]([N+:48]([O-:50])=[O:49])=[C:44]([CH3:51])[CH:43]=3)[C:34]=2[CH2:33]1)=[O:31]

Participants

5

Reactant 3

HCID 8333Diphenylacetic AcidHCID 14457530HCID 14457530, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 14403640HCID 14403640, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
2 °C

Procedure

A mixture of 16.7 g dicyclohexycarbodiimide, 10.9 g hydroxybenzotriazole hydrate, 17.2 g diphenylacetic acid and 150 mL acetonitrile is stirred at 2° C. for 15 min then treated with a solution of 25.4 g methyl-1-(3-methyl-4-nitrophenyl)methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylate in 125 mL acetonitrile. The resulting suspension is stirred 48 hr at 25° C., filtered and the filtrate is evaporated, dissolved in dichloromethane, washed with 10% Na2CO3, dried and evaporated. Chromatography on silica gel (chloroform-methanol, 99:1) gives a crisp foam which crystallizes when triturated with methanol. MS (FAB) 525 (M+1).

Workup

  1. stirringThe resulting suspension is stirred 48 hr at 25° C.
  2. filtrationfiltered
  3. customthe filtrate is evaporated
  4. dissolutiondissolved in dichloromethane
  5. washwashed with 10% Na2CO3
  6. customdried
  7. customevaporated
  8. customChromatography on silica gel (chloroform-methanol, 99:1) gives a crisp foam which
  9. customcrystallizes when
  10. customtriturated with methanol

Sources & evidence

ORD record
ord-7576e45b87404c868893595e43cace0e
Source dataset
uspto-grants-1989_03
Patent number
US04812462

Reaction notes

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