Pyridine → 1-Trityl-1H-imidazole-4-carboxylic acid

HRID 1874798Notes

Reaction equation

HRID 1874798 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([OH:8])=[O:7])[N:3]=[CH:2]1.[C:9](Cl)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CN(C=O)C.N1C=CC=CC=1>CCOC(C)=O.O>[C:10]1([C:9]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:1]2[CH:5]=[C:4]([C:6]([OH:8])=[O:7])[N:3]=[CH:2]2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 6456Trityl chlorideHCID 178524800HCID 178524800, compound

Product 1

HCID 105701171-Trityl-1H-imidazole-4-carboxylic acidYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(Triphenylmethyl)-1H-imidazole-4-carboxylic acid was prepared as described in J. Med. Chem. 2001, 44, 1268. 1H-Imidazole-4-carboxylic acid (0.50 g, 4.5 mmol) and trityl chloride (1.35 g, 4.9 mmol) were added to a solution of DMF (30 mL) and pyridine (15 mL) and stirred overnight. Water and EtOAc were added. The layers were separated and the aqueous layer extracted with EtOAc (2×50 mL). The organic extracts were combined, washed with water and brine, dried over Na2SO4, filtered and evaporated. The oil was triturated with EtOAc to afford the title compound (1.5 g, 95%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 12.40 (br. s., 1H), 7.42 (t, 9H), 7.17-7.35 (m, 2H), 7.10 (d, 6H). MS: m/z 111 (M−243).

Workup

  1. custom1-(Triphenylmethyl)-1H-imidazole-4-carboxylic acid was prepared
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted with EtOAc (2×50 mL)
  4. washwashed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe oil was triturated with EtOAc

Sources & evidence

ORD record
ord-04dc42dbad9d486e9a019c76721be053
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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