Triethylamine → HCID 22254544, compound

HRID 1611703Notes

Reaction equation

HRID 1611703 reaction equation
[CH3:1][CH:2]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([NH2:19])[CH:15]=[CH:14]2)[CH2:3][C:4]([CH3:7])([CH3:6])[CH3:5].CCN(CC)CC.[CH3:27][C:28]([CH3:33])([CH3:32])[C:29](Cl)=[O:30]>C1COCC1>[CH3:27][C:28]([CH3:33])([CH3:32])[C:29]([NH:19][C:16]1[CH:15]=[CH:14][C:13]2[C:18](=[C:9]([O:8][CH:2]([CH3:1])[CH2:3][C:4]([CH3:7])([CH3:6])[CH3:5])[CH:10]=[CH:11][CH:12]=2)[N:17]=1)=[O:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 10083869HCID 10083869, compound

Product 1

HCID 22254544HCID 22254544, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 20 mL scintillation vial was added a stir bar, the title compound from Example 16 (161 mg, 0.624 mmol) and 1.5 mL of THF. To the resultant solution was added Et3N (0.174 mL, 2 equiv) and trimethylacetylchloride (93 μL, 1.2 equiv). The solution was allowed to stir overnight, after which time the mixture placed directly on a silica column and eluted with EtOAc/hexanes to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.27 (m, 1H), 7.96–8.18 (m, 1H), 7.42 (m, 2H), 7.21 (m, 1H), 4.64–4.90 (m, 1H), 1.90 (m, 1H), 1.53 (m, 1H), 1.31 (m, 12H), 0.83–1.05 (m, 9H); MS (DCI/NH3) m/z 343 [M+H]+.

Workup

  1. additionTo a 20 mL scintillation vial was added a stir bar
  2. washeluted with EtOAc/hexanes

Sources & evidence

ORD record
ord-337499fcb8fe418392fd481d9d119337
Source dataset
uspto-grants-2006_01
Patent number
US06989392B2

Reaction notes

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