Trityl chloride → HCID 70982312, compound

HRID 1409374Notes

Reaction equation

HRID 1409374 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[CH:10]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:8][N:7]=2)[N:3]=[CH:2]1.[C:16]1([C:22](Cl)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C>C(Cl)Cl>[C:22]([N:1]1[CH:5]=[C:4]([C:6]2[CH:10]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:8][N:7]=2)[N:3]=[CH:2]1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 6456Trityl chloride3×HCID 8471Triethylamine2×HCID 178468660HCID 178468660, compound

Product 1

HCID 70982312HCID 70982312, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Ethyl 3-(1H-imidazol-4-yl)-1H-pyrazole-5-carboxylate (6.79 mmol, 1.4 g) was suspended in DCM (20 ml) under nitrogen atmosphere. Triphenylmethyl chloride (8.15 mmol, 2.271 g) was added and stirred for 10 min at RT. Triethylamine (8.15 mmol, 1.136 ml) was added and the resulting mixture was stirred for 20 h at RT after which DCM (10 ml) and triphenylmethyl chloride (1 g) was added. The stirring was continued for another 4.5 days. More triphenylmethyl chloride (1.14 g) and triethylamine (0.6 ml) was added and the mixture was stirred for another day. The mixture was diluted with DCM and washed with NaHCO3. The organic phase was dried, filtered and evaporated. The residue was purified by trituration from ACN. 1.837 g of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 1.28 (t, 3H), 4.25 (q, 2H), 6.89 (s, 1H), 7.09-7.18 (m, 6H), 7.18-7.33 (m, 6H), 7.36-7.47 (m, 3H), 7.50 (s, 1H), 7.55 (s, 1H), 13.63 (bs, 1H).

Workup

  1. additionwas added
  2. waitThe stirring was continued for another 4.5 days
  3. stirringthe mixture was stirred for another day
  4. washwashed with NaHCO3
  5. customThe organic phase was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by trituration from ACN

Sources & evidence

ORD record
ord-c67eb90901b349ac8ad43d7b754f84dd
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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