Tetrahydrofuran → HCID 69127458, compound

HRID 2064196Notes

Reaction equation

HRID 2064196 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[C:5]([CH3:10])=[CH:4][C:3]=1[NH:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1.[O:25]1CCC[CH2:26]1>>[C:8]([C:6]1[C:5]([CH3:10])=[CH:4][C:3]2[N:11]([CH:12]3[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17]3)[C:26](=[O:25])[NH:1][C:2]=2[CH:7]=1)#[N:9]

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 69127637HCID 69127637, compound

Product 1

HCID 69127458HCID 69127458, compoundYield 100%

Conditions

Temperature
50 °C

Procedure

A solution of 1,1-dimethylethyl 4-[(2-amino-4-cyano-5-methylphenyl)amino]-1-piperidinecarboxylate (D92) (2.55 mmol, 840 mg) in tetrahydrofuran (8 mL) was treated with N,N′-carbonyldiimidazole (3.83 mmol, 613 mg, 1.5 eq) under argon at room temperature, then the mixture was heated at 50° C. for 1 h, concentrated under reduced pressure, and the residue was treated with 10% aqueous sodium carbonate solution and extracted twice with ethyl acetate. The organics were combined, dried and concentrated under reduced pressure to give the title compound (3.23 mmol, 1.15 g, >100% yield). M+H 357.3, 301.2 (full molecule and fragment for loss of the tert-butyl group).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionthe residue was treated with 10% aqueous sodium carbonate solution
  3. extractionextracted twice with ethyl acetate
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-97b861cf384d4ed191f2791b77aea861
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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