Diisopropylethylamine → HCID 59783673, compound

HRID 1946619Notes

Reaction equation

HRID 1946619 reaction equation
C1([C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[C:5]=2[NH2:11])CC1.C(N([CH:18]([CH3:20])[CH3:19])CC)(C)C.[Cl:21][C:22]1[N:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24](Cl)=[O:25]>C1COCC1>[Cl:21][C:22]1[N:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24]([NH:11][C:5]1[CH:4]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:10][CH:18]1[CH2:20][CH2:19]1)=[O:25]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27745412-Chloronicotinoyl chlorideHCID 68945551HCID 68945551, compound

Product 1

HCID 59783673HCID 59783673, compoundYield 516.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of title compound 381 (0.83 g, 5.84 mmol) and diisopropylethylamine (1.02 mL, 0.74 mmol) in THF (50 mL) was added a solution of 2-chloronicotinoyl chloride (1.03 g, 5.84 mmol) in THF at 0° C. The reaction mixture was stirred over night and concentrated. To the residue was added a saturated solution of bicarbonate (3 mL) and this aqueous layer was extracted with DCM (2×). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated. The solid was triturated in DCM (3 mL) and filtered. The filtrate was evaporated and purified by flash chromatography (0% to 80% ethyl acetate in hexanes). The 2 solids were mixed to afford title compound 382 (1.1 g, 65%) as a white solid. MS (m/z): 288.0 (M+H).

Workup

  1. concentrationconcentrated
  2. additionTo the residue was added a saturated solution of bicarbonate (3 mL)
  3. extractionthis aqueous layer was extracted with DCM (2×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe solid was triturated in DCM (3 mL)
  9. filtrationfiltered
  10. customThe filtrate was evaporated
  11. custompurified by flash chromatography (0% to 80% ethyl acetate in hexanes)
  12. additionThe 2 solids were mixed

Sources & evidence

ORD record
ord-5ccb6853f33047c2a7ed0d0ed7a8c313
Source dataset
uspto-grants-2013_03
Patent number
US08399452B2

Reaction notes

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