Triethylamine → HCID 86665192, compound

HRID 406531Notes

Reaction equation

HRID 406531 reaction equation
Cl[C:2]1[C:3]2[C@:10]3([CH2:25][C:13]4=[N:14][CH:15]=[C:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:17]=[C:12]4[CH2:11]3)[C:9](=[O:26])[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.C(N(CC)CC)C.[H][H]>C(OCC)(=O)C.[Pd]>[O:26]=[C:9]1[NH:8][C:4]2[N:5]=[CH:6][N:7]=[CH:2][C:3]=2[C@@:10]21[CH2:25][C:13]1=[N:14][CH:15]=[C:16]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[CH:17]=[C:12]1[CH2:11]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 86665191HCID 86665191, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86665192HCID 86665192, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl (6S)-4′-chloro-6′-oxo-5,6′,7,7′-tetrahydrospiro[cyclopenta[b]pyridine-6,5′-pyrrolo[2,3-d]pyrimidine]-3-carboxylate (200 mg, 0.537 mmol) in dry ethyl acetate (5.37 mL) was added triethylamine (299 μL, 2.15 mmol) and palladium on carbon (571 mg, 10%, 0.537 mmol). The reaction was placed on a Parr apparatus at 50 psi hydrogen gas. After 16 h, the reaction mixture was filtered under a nitrogen atmosphere through Celite®, washing with ethyl acetate. The filtrate was concentrated to give the title compound, along with one equivalent of triethylamine hydrochloride. MS: m/z=339.3 (M+1).

Workup

  1. filtrationthe reaction mixture was filtered under a nitrogen atmosphere through Celite®
  2. washwashing with ethyl acetate
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-1a9f888d2bd345dbb39d2eb7b9d1a616
Source dataset
uspto-grants-2014_06
Patent number
US08754096B2

Reaction notes

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