Triethylamine hydrochloride → Hydrochloric Acid

HRID 1404480Notes

Reaction equation

HRID 1404480 reaction equation
[O:1]=[C:2]1[NH:10][C:5]2[N:6]=[CH:7][N:8]=[CH:9][C:4]=2[C@@:3]21[CH2:25][C:13]1=[N:14][CH:15]=[C:16]([C:18]([O:20]C(C)(C)C)=[O:19])[CH:17]=[C:12]1[CH2:11]2.[ClH:26].[CH2:27]([N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])[CH3:28]>Cl>[O:1]=[C:2]1[NH:10][C:5]2[N:6]=[CH:7][N:8]=[CH:9][C:4]=2[C@@:3]21[CH2:25][C:13]1=[N:14][CH:15]=[C:16]([C:18]([OH:20])=[O:19])[CH:17]=[C:12]1[CH2:11]2.[ClH:26].[ClH:26].[CH2:27]([N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])[CH3:28]

Participants

6

Reactant 2

HCID 11130Triethylamine hydrochlorideHCID 86665192HCID 86665192, compound

Product 3

HCID 313Hydrochloric AcidHCID 11130Triethylamine hydrochlorideHCID 68746693HCID 68746693, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To solid tert-butyl (6S)-6′-oxo-5,6′,7,7′-tetrahydrospiro[cyclopenta[b]pyridine-6,5′-pyrrolo[2,3-d]pyrimidine]-3-carboxylate (255 mg, 0.536 mmol) containing one equivalent of triethylamine hydrochloride (from previous step) was added hydrochloric acid solution (20 mL, 4 M in dioxane). After 16 h, the mixture was concentrated to give the title compound as a bis hydrochloric acid salt with one equivalent of triethylamine hydrochloride. MS: m/z=283.2 (M+1). 1H NMR (500 MHz, DMSO): δ 11.75 (s, 1H); 9.50 (s, 1H); 8.90 (s, 1H); 8.80 (s, 1H); 8.40 (s, 1H); 8.20 (s, 1H); 3.50-3.40 (m, 4H).

Workup

  1. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-254eb972348b40ddb0e37cb0d4471358
Source dataset
uspto-grants-2014_12
Patent number
US08912210B2

Reaction notes

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