Pyridine → HCID 66953299, compound

HRID 1424604Notes

Reaction equation

HRID 1424604 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[NH2:14][C:15](=O)[CH2:16][CH:17]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:19]2([CH2:24][CH2:23][N:22]([C:25]([NH:27][CH:28]3[CH:35]4CC5C[CH:33]([CH2:37][CH:29]3C5)[CH2:34]4)=[O:26])[CH2:21][CH2:20]2)[CH2:18]1.N1C=CC=CC=1>O1CCOCC1.O>[C:15]([CH2:16][CH:17]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:19]2([CH2:24][CH2:23][N:22]([C:25]([NH:27][CH:28]3[CH2:35][CH2:34][CH2:33][CH2:37][CH2:29]3)=[O:26])[CH2:21][CH2:20]2)[CH2:18]1)#[N:14]

Participants

6

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 58137246HCID 58137246, compound

Product 1

HCID 66953299HCID 66953299, compoundYield 20.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of trifluoroacetic anhydride (39 mg, 0.18 mmol) in dioxane (2 mL) was added dropwise to a stirred, ice-cooled solution of (±)-3-(2-amino-2-oxoethyl)-N-(2-adamantyl)-2,3-dihydrospiro[indene-1,4′-piperidine]-1′-carboxamide (60 mg, 0.14 mmol) and pyridine (63 mg, 0.28 mmol). The reaction mixture was stirred at rt overnight. The mixture was diluted with water and extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2SO4, and concentrated. The crude product was purified by preparative TLC to afford (±)-3-(cyanomethyl)-N-cyclohexyl-2,3-dihydrospiro[indene-1,4′-piperidine]-1′-carboxamide (10 mg, 18%). LC-MS Method 5 tR=1.508 min, m/z=404.2; 1H NMR (CDCl3) δ=1.60-1.73 (m, 5H), 1.77-1.82 (m, 5H), 1.85-1.94 (m, 2H), 2.07-2.14 (m, 1H), 2.51-2.62 (m, 3H), 2.71-2.83 (m, 114), 2.98-3.10 (m, 2H), 3.46-3.55 (m, 1H), 3.82-3.94 (m, 3H), 7.10-7.15 (m, 1H), 7.20-7.28 (m, 3H).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by preparative TLC

Sources & evidence

ORD record
ord-ed74caa0edee437099c6c135cd818405
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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