Diisopropylethylamine → HCID 68291273, compound

HRID 1507948Notes

Reaction equation

HRID 1507948 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](Cl)=[C:8]([C:11]([NH2:13])=[O:12])[CH:7]=[N:6][N:5]2[CH:14]=1.Cl.[NH2:16][CH:17]([CH3:25])[C:18]([CH3:24])([CH3:23])[C:19]([O:21][CH3:22])=[O:20].CCN(C(C)C)C(C)C>CC(N(C)C)=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([NH:16][CH:17]([CH3:25])[C:18]([CH3:24])([CH3:23])[C:19]([O:21][CH3:22])=[O:20])=[C:8]([C:11](=[O:12])[NH2:13])[CH:7]=[N:6][N:5]2[CH:14]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 682911926-Bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamideHCID 889241621400877-67-9

Product 1

HCID 68291273HCID 68291273, compoundYield 50.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 6-bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide (Preparation 5, 1.0 gm, 3.64 mmol) and methyl 3-amino-2,2-dimethylbutanoate hydrochloride (1.0 g, 5.50 mmol) in DMA (10 ml) was added DIPEA (3.14 ml, 18.2 mmol) at rt. The reaction mixture was stirred at 110° C. overnight. Upon completion, the reaction mixture was cooled to rt and DMA was removed under reduced pressure to give a dark oily compound. It was dissolved in ethyl acetate (50 ml) and washed with water (20 ml). The aqueous layer was extracted with ethyl acetate (3×50 ml). The combined organic layers were washed with brine (50 ml), dried over anhyd. sodium sulfate, filtered and concentrated under vacuum. The crude compound was purified by column chromatography using 40% ethyl acetate in hexanes as the eluting solvent to give the title compound (700 mg, 50%). 1NMR (400 MHz, DMSO-d6): δ 1.22-1.24 (m, 9H), 3.57-3.574 (s,3H), 4.47-4.51 (m, 1H), 7.046 (s, 1H), 7.89 (s, 1H), 8.24 (s, 1H), 10.92-10.94 (d, J=9.2 Hz).

Workup

  1. temperatureUpon completion, the reaction mixture was cooled to rt
  2. customDMA was removed under reduced pressure
  3. customto give a dark oily compound
  4. washwashed with water (20 ml)
  5. extractionThe aqueous layer was extracted with ethyl acetate (3×50 ml)
  6. washThe combined organic layers were washed with brine (50 ml)
  7. customdried over anhyd
  8. filtrationsodium sulfate, filtered
  9. concentrationconcentrated under vacuum
  10. customThe crude compound was purified by column chromatography

Sources & evidence

ORD record
ord-eec5f4ddf88449e9a176bab3b67b43d5
Source dataset
uspto-grants-2015_12
Patent number
US09221826B2

Reaction notes

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