Diisopropylethylamine → HCID 59783673, compound

HRID 718087Notes

Reaction equation

HRID 718087 reaction equation
[CH:1]1([NH:4][C:5]2[C:6]([NH2:11])=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:3][CH2:2]1.C(N(C(C)C)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:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[NH:4][CH:1]1[CH2:3][CH2:2]1)=[O:25]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27745412-Chloronicotinoyl chlorideHCID 10582926N-cyclopropylbenzene-1,2-diamine

Product 1

HCID 59783673HCID 59783673, compoundYield 65.5%

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-ea10bc6506a04c7eaf58c4d0a0ce8016
Source dataset
uspto-grants-2015_11
Patent number
US09193749B2

Reaction notes

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