Diisopropylethylamine → HCID 69127906, compound

HRID 2064194Notes

Reaction equation

HRID 2064194 reaction equation
F[C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:13])[CH:3]=1.[NH2:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[C:6]([C:5]1[C:4]([CH3:13])=[CH:3][C:2]([NH:14][CH:15]2[CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:19][CH2:20]2)=[C:9]([N+:10]([O-:12])=[O:11])[CH:8]=1)#[N:7]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 573458874-Fluoro-2-methyl-5-nitrobenzonitrile

Product 1

HCID 69127906HCID 69127906, compoundYield 110%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 4-fluoro-2-methyl-5-nitrobenzonitrile (D90) (3 mmol, 540.3 mg) in dimethylformamide (20 mL) was treated with 1,1-dimethylethyl 4-amino-1-piperidinecarboxylate (3 mmol, 600.9 mg, 1 eq) and diisopropylethylamine (3 mmol, 387.6 mg, 1 eq) under argon at room temperature and then heated at 80° C. overnight. The mixture was then concentrated under reduced pressure then treated with 10% aqueous sodium carbonate solution and extracted with ether/ethyl acetate. The organics were dried and concentrated under reduced pressure to give the title compound as a solid (3.3 mmol, 1.19 mg, >100% yield). M+H 304.97 for main fragment (loss of tert-butyl group).

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. additionthen treated with 10% aqueous sodium carbonate solution
  3. extractionextracted with ether/ethyl acetate
  4. customThe organics were dried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7a9ebbb0ade3447d8b27e657867df41a
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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