Diphenylacetic Acid → HCID 21249260, compound

HRID 1195010Notes

Reaction equation

HRID 1195010 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.Cl.Cl.[CH3:30][O:31][C:32]([CH:34]1[NH:39][CH2:38][C:37]2[N:40]([CH2:43][C:44](=[O:51])[C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[CH:41]=[N:42][C:36]=2[CH2:35]1)=[O:33].C(N(C(C)C)CC)(C)C>C(#N)C>[CH3:30][O:31][C:32]([CH:34]1[N:39]([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)[CH2:38][C:37]2[N:40]([CH2:43][C:44](=[O:51])[C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[CH2:41][NH:42][C:36]=2[CH2:35]1)=[O:33]

Participants

6

Reactant 4

HCID 8333Diphenylacetic AcidHCID 81531DiisopropylethylamineHCID 14403665HCID 14403665, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 21249260HCID 21249260, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent3×

Conditions

Temperature
25 °C

Procedure

A mixture of 9.3 g dicyclohexycarbodiimide, 6.1 g hydroxybenzotriazole hydrate, 9.5 g diphenylacetic acid and 100 mL acetonitrile is stirred at 25° C. for 15 min (suspension A). A mixture of 15.8 g methyl-3-(2-oxo-2-phenylethyl)-4,5,6,7-tetrahydro-3H-imidazo-[4,5-c]pyridine-6-carboxylate dihydrochloride, 14.8 mL diisopropylethylamine and 100 mL acetonitrile is stirred 10 min at 25° C. then treated with suspension A, using 100 mL acetonitrile to complete the transfer. The resulting suspension is stirred 48 hr, 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 methyl-5-diphenylacetyl-3-(2-oxo-2-phenylethyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylate as foam. MS (FAB) 494 (M+1).

Workup

  1. stirringis stirred 10 min at 25° C.
  2. additionthen treated with suspension A,
  3. stirringThe resulting suspension is stirred 48 hr
  4. filtrationfiltered
  5. customthe filtrate is evaporated
  6. dissolutiondissolved in dichloromethane
  7. washwashed with 10% Na2CO3
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-18b07f3c049f4ef8a569576ceb5956d6
Source dataset
uspto-grants-1989_03
Patent number
US04816463

Reaction notes

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