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

HRID 1478987Notes

Reaction equation

HRID 1478987 reaction equation
[ClH:1].C(OC([N:9]1[CH2:23][C:12]2=[C:13]3[N:18]([N:19]=[C:11]2[CH2:10]1)[C:17]([CH3:20])=[C:16]([CH3:21])[C:15]([CH3:22])=[N:14]3)=O)(C)(C)C>O1CCOCC1>[ClH:1].[CH3:22][C:15]1[C:16]([CH3:21])=[C:17]([CH3:20])[N:18]2[C:13]([N:14]=1)=[C:12]1[CH2:23][NH:9][CH2:10][C:11]1=[N:19]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 896438935,6,7-trimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carboxylic acid tert-butyl ester

Product 1

HCID 896439905,6,7-trimethyl-2,3-dihydro-1H-2,4,7a,8-tetraaza-cyclopenta[a]indene hydrochlorideYield 82%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A 4M solution of HCl in 1,4-dioxane (1.24 mL; 4.96 mmol; 15 eq.) was added to a solution of 5,6,7-trimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carboxylic acid tert-butyl ester (100 mg; 0.33 mmol; 1 eq.) in 1,4-dioxane (5 mL) and the resulting mixture was stirred at room temperature for 18 hours. The solvent was evaporated in vacuo and the residue was triturated in 1,4-dioxane. Concentration to dryness afforded the title compound (65 mg, 82%) as a white solid. 1H NMR (DMSO-d6) δ 10.40-10.30 (m, 1H), 4.57-4.50 (m, 4H), 2.73 (s, 3H), 2.54 (s, 3H), 2.28 (s, 3H). HPLC (max plot) 100.0%; Rt 1.26 min. UPLC/MS: (MS+) 203.1 ([M+H]+).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was triturated in 1,4-dioxane
  3. concentrationConcentration to dryness

Sources & evidence

ORD record
ord-4d53fc6ac41448eca3ca006e3e3bdb9b
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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