Triethylamine → HCID 67334794, compound

HRID 1669859Notes

Reaction equation

HRID 1669859 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:13]=[C:12]([CH:14]3[CH2:19][CH2:18][N:17]([C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:16][CH2:15]3)[N:11]([CH2:26][C:27]3[CH:40]=[CH:39][C:30]([C:31](NC4NN=NN=4)=[O:32])=[CH:29][CH:28]=3)[N:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(N(CC)CC)C.CC(C)(C)C(Cl)=[O:51].[OH-].[Na+]>C(Cl)Cl.C1COCC1.CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:13]=[C:12]([CH:14]3[CH2:15][CH2:16][N:17]([C:20](=[O:25])[C:21]([CH3:22])([CH3:24])[CH3:23])[CH2:18][CH2:19]3)[N:11]([CH2:26][C:27]3[CH:40]=[CH:39][C:30]([C:31]([OH:51])=[O:32])=[CH:29][CH:28]=3)[N:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 62493Pivaloyl chlorideHCID 178447187HCID 178447187, compound

Product 1

HCID 67334794HCID 67334794, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the intermediate from step F (100 mg, 0.225 mmol) in DCM (3 mL) was added triethyl amine (94 μl, 0.675 mmol) followed by trimethyl acetyl chloride (33.25 μL, 0.27 mmol). After 2 hours the reaction was diluted with DCM (10 mL) and washed with 1N HCl, saturated Na2CO3, dried over brine and concentrated in vacuo to give a colorless oil. This material was dissolved in THF (2 mL) and MeOH (1 mL) and 2N NaOH (2 mL) were added and the reaction left stirring at room temperature for 16 hours. The reaction was concentrated in vacuo. The residue was suspended in 1N HCl (until the pH was less then 2). The resulting suspension was extracted with EtOAc (3×), dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give the title compound as a white solid. 1H NMR (DMSO, 500 MHz): δ 7.93 (d, J=8.2 Hz, 2H), 7.81 (d, J=1.8 Hz, 2H), 7.51 (t, J=2.1 Hz, 1H), 7.26 (d, J=8.3 Hz, 2H), 6.94 (s, 1H), 5.54 (s, 2H), 4.34 (d, J=13.3 Hz, 2H), 3.0 (m, 1H), 2.86 (t, J=12.9 Hz, 2H), 2.51 (t, J=1.6 Hz, 1H), 1.74 (d, J=11 Hz, 2H), 1.44 (dq, J=3.4, 12.8 Hz, 2H), 1.2 (s, 9H).

Workup

  1. washwashed with 1N HCl, saturated Na2CO3
  2. dry with materialdried over brine
  3. concentrationconcentrated in vacuo
  4. customto give a colorless oil
  5. waitthe reaction left
  6. concentrationThe reaction was concentrated in vacuo
  7. extractionThe resulting suspension was extracted with EtOAc (3×)
  8. dry with materialdried over anhydrous Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-292c99b263d7440ea19a0c16592916b1
Source dataset
uspto-grants-2011_08
Patent number
US07989475B2

Reaction notes

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