Diisopropylethylamine → HCID 86646070, compound

HRID 1800673Notes

Reaction equation

HRID 1800673 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:21]=[CH:22][CH:23]=1)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([NH:18][CH:19]=O)[CH:13]=1)=[O:10])([CH3:5])[CH3:4])#[N:2].C(N(C(C)C)C(C)C)C.ClC1[N:39]=[C:38]([S:40][C:41]#[N:42])[C:37]([N+:43]([O-:45])=[O:44])=[CH:36][N:35]=1.C(=O)([O-])O.[Na+]>O1CCCC1>[C:1]([C:3]([C:6]1[CH:7]=[C:8]([C:9]([NH:11][C:12]2[CH:13]=[C:14]([NH:18][C:19]3[N:39]=[C:38]([S:40][C:41]#[N:42])[C:37]([N+:43]([O-:45])=[O:44])=[CH:36][N:35]=3)[CH:15]=[CH:16][CH:17]=2)=[O:10])[CH:21]=[CH:22][CH:23]=1)([CH3:5])[CH3:4])#[N:2]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 210775882-Chloro-5-nitropyrimidin-4-yl thiocyanateHCID 86646069HCID 86646069, compound

Product 1

HCID 86646070HCID 86646070, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(1-cyano-1-methylethyl)-N-[3-(formylamino)phenyl]benzamide (676 mg, 2.42 mmol) in tetrahydrofuran (10 mL) were added N-ethyl-N-isopropylpropane-2-amine (643 μL, 3.63 mmol) and 2-chloro-5-nitropyrimidin-4-yl thiocyanate (576 mg, 2.66 mmol), and the mixture was stirred at room temperature for 30 min. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution (30 mL), and the mixture was extracted with ethyl acetate (30 mL, 10 mL). The combined organic layer was washed with saturated brine (5 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was washed with ethyl acetate to give the title compound (933 mg, 84%) as a yellow solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (30 mL, 10 mL)
  2. washThe combined organic layer was washed with saturated brine (5 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe insoluble material was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. washThe obtained residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-a171c67e1ab842728d161b438fbed340
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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