Hydrochloric Acid → 6-ethyl-5,7-dimethyl-2,3-dihydro-1H-2,4,7a,8-tetraaza-cyclopenta[a]indene

HRID 1478988Notes

Reaction equation

HRID 1478988 reaction equation
C(OC([N:8]1[CH2:15][C:14]2[C:10](=[N:11][NH:12][C:13]=2[NH2:16])[CH2:9]1)=O)(C)(C)C.[CH2:17]([CH:19]([C:23](=O)[CH3:24])[C:20](=O)[CH3:21])[CH3:18].Cl>CC(O)=O>[CH2:23]([C:19]1[C:20]([CH3:21])=[N:16][C:13]2[N:12]([N:11]=[C:10]3[CH2:9][NH:8][CH2:15][C:14]3=2)[C:17]=1[CH3:18])[CH3:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 737613-Ethylpentane-2,4-dioneHCID 178451527HCID 178451527, compound

Product 1

HCID 896528476-ethyl-5,7-dimethyl-2,3-dihydro-1H-2,4,7a,8-tetraaza-cyclopenta[a]indeneYield 94%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3-amino-2,6-dihydro-4H-pyrrolo[3,4-c]pyrazole-5-carboxylic acid tert-butyl ester (0.6 g; 2.68 mmol; 1 eq.) and 3-ethyl-2,4-pentanedione (0.36 mL; 2.68 mmol; 1 eq.) in AcOH (8 mL) was stirred at room temperature for 32 hours. Aq. 32% HCl (1.05 mL; 10.7 mmol; 4 eq.) was added and the resulting mixture stirred for a further 16 hours. After concentration in vacuo, the residue was triturated in MTBE and the precipitate filtered off and dried. The solid was taken up in ethyl acetate and washed with 1M aq. NaOH (2×), dried over magnesium sulfate and concentrated in vacuo to afford the title compound (450 mg, 94%) as a beige solid. 1H NMR (DMSO-d6) δ 4.05-4.00 (m, 4H), 2.73-2.63 (m, 5H), 2.51 (s, 3H), 1.12 (t, J=7.4 Hz, 3H). UPLC/MS: (MS+) 217.3 ([M+H]+).

Workup

  1. stirringthe resulting mixture stirred for a further 16 hours
  2. concentrationAfter concentration in vacuo
  3. customthe residue was triturated in MTBE
  4. filtrationthe precipitate filtered off
  5. customdried
  6. washwashed with 1M aq. NaOH (2×)
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5fb68c0a50a04e44b9a566e7e028465b
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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