Diisopropylethylamine → HCID 86646072, compound

HRID 1800678Notes

Reaction equation

HRID 1800678 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:20]=[CH:21][CH:22]=1)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([NH:18][CH3:19])[CH:13]=1)=[O:10])([CH3:5])[CH3:4])#[N:2].C(N(C(C)C)C(C)C)C.Cl[C:33]1[N:38]=[C:37]([S:39][C:40]#[N:41])[C:36]([N+:42]([O-:44])=[O:43])=[CH:35][N:34]=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]([N:18]([CH3:19])[C:33]3[N:38]=[C:37]([S:39][C:40]#[N:41])[C:36]([N+:42]([O-:44])=[O:43])=[CH:35][N:34]=3)[CH:15]=[CH:16][CH:17]=2)=[O:10])[CH:20]=[CH:21][CH:22]=1)([CH3:5])[CH3:4])#[N:2]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 210775882-Chloro-5-nitropyrimidin-4-yl thiocyanateHCID 68415693HCID 68415693, compound

Product 1

HCID 86646072HCID 86646072, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the above-mentioned crude product of 3-(1-cyano-1-methylethyl)-N-[3-(methylamino)phenyl]benzamide in tetrahydrofuran (15 mL) were added N-ethyl-N-isopropylpropane-2-amine (345 μL, 1.98 mmol) and 2-chloro-5-nitropyrimidin-4-yl thiocyanate (314 mg, 1.50 mmol), and the mixture was stirred at room temperature for 1.5 hr. 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 (10 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 purified by silica gel column chromatography (hexane/ethyl acetate=85/15→70/30), and the fractions containing the object product were concentrated under reduced pressure to give 2-{[3-({[3-(1-cyano-1-methylethyl)phenyl]carbonyl}amino)phenyl](methyl)amino}-5-nitropyrimidin-4-yl thiocyanate as a yellow oil. The obtained compound was used for the next reaction without further purification.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (30 mL, 10 mL)
  2. washThe combined organic layer was washed with saturated brine (10 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. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=85/15→70/30)
  7. additionthe fractions containing the object product
  8. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-bb0c41469a8b4fdab925988c083cfa19
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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