Diisopropylethylamine → HCID 68358957, compound

HRID 1408966Notes

Reaction equation

HRID 1408966 reaction equation
CCN(C(C)C)C(C)C.[Br:10][C:11]1[CH:12]=[C:13]2[C:18](Cl)=[C:17]([C:20]([NH2:22])=[O:21])[CH:16]=[N:15][N:14]2[CH:23]=1.[NH2:24][C@@H:25]1[CH2:29][CH2:28][C@:27]([CH3:34])([C:30]([O:32][CH3:33])=[O:31])[C:26]1([CH3:36])[CH3:35]>CN1C(=O)CCC1.C(OCC)(=O)C>[Br:10][C:11]1[CH:12]=[C:13]2[C:18]([NH:24][C@@H:25]3[CH2:29][CH2:28][C@:27]([CH3:34])([C:30]([O:32][CH3:33])=[O:31])[C:26]3([CH3:36])[CH3:35])=[C:17]([C:20](=[O:21])[NH2:22])[CH:16]=[N:15][N:14]2[CH:23]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 682911926-Bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamideHCID 86707713HCID 86707713, compound

Product 1

HCID 68358957HCID 68358957, compoundYield 57.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

Hunig's base (1.27 mL, 7.29 mmol) was added to a solution of 6-bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide (Preparation 5, 625 mg, 2.277 mmol) and (1S,3R)-methyl 3-amino-1,2,2-trimethylcyclopentanecarboxylate (464 mg, 2.505 mmol) in NMP (5692 n1). The reaction was heated at 90° C. for 14 hrs. The reaction was cooled to room temperature and diluted with ethyl acetate (20 ml). The ethyl acetate solution was washed with water (3×10 ml), dried with sodium sulfate, filtered, and concentrated under reduced pressure to give a light yellow oil. The crude product was chromatographed on the silica gel column eluted with 0-50% ethyl acetate in hexane to afford the title compound (583 mg, 1.308 mmol, 57.5% yield) as a white solid. LC/MS found [M+H]+=425.1. 1H NMR (400 MHz, MeOD) δ ppm 8.13 (1 H, s), 7.60-7.66 (1 H, m), 6.88-6.95 (1 H, m), 4.43-4.52 (1 H, m), 3.71 (3 H, s), 2.62-2.71 (1 H, m), 2.31-2.39 (1 H, m), 1.65-1.76 (1 H, m), 1.55-1.64 (1 H, m), 1.32 (3 H, s), 1.09 (3 H, s), 0.98 (3 H, s).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. washThe ethyl acetate solution was washed with water (3×10 ml)
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give a light yellow oil
  7. customThe crude product was chromatographed on the silica gel column
  8. washeluted with 0-50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-13ceccfb8e8f496c96f20d1866842700
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

Loading…