Triethylamine → Triethylamine hydrochloride

HRID 588973Notes

Reaction equation

HRID 588973 reaction equation
[Cl:1][C:2]1[C:3]2[C@@:10]3([CH2:18][C:17]4[C:12](=[CH:13][CH:14]=[C:15]([C:19]([O:21][CH3:22])=[O:20])[CH:16]=4)[CH2:11]3)[C:9](=[O:23])[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH2:24]([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])[CH3:25]>CCOC(C)=O.[Pd]>[O:23]=[C:9]1[NH:8][C:4]2[N:5]=[CH:6][N:7]=[CH:2][C:3]=2[C@:10]21[CH2:18][C:17]1[C:12](=[CH:13][CH:14]=[C:15]([C:19]([O:21][CH3:22])=[O:20])[CH:16]=1)[CH2:11]2.[ClH:1].[CH2:24]([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])[CH3:25]

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 86695346Methyl (2R)-4'-chloro-6'-oxo-1,3,6',7'-tetrahydrospiro[indene-2,5'-pyrrolo[2,3-d]pyrimidine]-5-carboxylate

Product 2

HCID 11130Triethylamine hydrochlorideHCID 69965261Methyl (2R)-6'-oxo-1,3,6',7'-tetrahydrospiro[indene-2,5'-pyrrolo[2,3-d]pyrimidine]-5-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl (2R)-4′-chloro-6′-oxo-1,3,6′,7′-tetrahydrospiro[indene-2,5′-pyrrolo[2,3-d]pyrimidine]-5-carboxylate (860 mg, 2.61 mmol) and triethylamine (364 μL, 2.61 mmol) in 10 mL of EtOAc was added 2.6 g of 10% palladium on carbon. The reaction was placed under 50 psi of H2 and shaken on a Parr hydrogenation apparatus. After 16 h, the reaction was backfilled with nitrogen, filtered through Celite® and concentrated in vacuo to afford the title compound as a mixture with 1 equivalent of triethylamine hydrochloride. MS: m/z=296.1 (M+1).

Workup

  1. filtrationfiltered through Celite®
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3960a8d813db42d5aaa15bf4328391ed
Source dataset
uspto-grants-2016_01
Patent number
US09227973B2

Reaction notes

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