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

HRID 1478995Notes

Reaction equation

HRID 1478995 reaction equation
[ClH:1].O1CCOCC1.C(OC([N:15]1[CH2:28][C:18]2=[C:19]3[N:24]([N:25]=[C:17]2[CH2:16]1)[C:23]([CH3:26])=[C:22]([CH3:27])[CH:21]=[N:20]3)=O)(C)(C)C>CO>[ClH:1].[ClH:1].[CH3:27][C:22]1[CH:21]=[N:20][C:19]2[N:24]([N:25]=[C:17]3[CH2:16][NH:15][CH2:28][C:18]3=2)[C:23]=1[CH3:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 896439196,7-dimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carboxylic acid tert-butyl ester

Product 1

HCID 1317365426,7-dimethyl-2,3-dihydro-1H-2,4,7a,8-tetraaza-cyclopenta[a]indene bis hydrochlorideYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 4M solution of HCl in 1,4-dioxane (10 mL; 40 mmol; 82.4 eq.) was added to a solution 6,7-dimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carboxylic acid tert-butyl ester (140 mg; 0.49 mmol; 1 eq.) in MeOH (2 mL) and the resulting mixture was stirred at room temperature for 18 hours then concentrated in vacuo. The residue was triturated in EtOH and the precipitate filtered off and dried to afford the title compound (78 mg, 62%) as a pale yellow solid. 1H NMR (DMSO-d6) δ 10.39 (br s, 2H), 8.91 (d, J=0.9 Hz, 1H), 6.24 (br s, 1H), 4.51-4.48 (m, 4H), 2.49 (s, 3H), 2.26 (s, 3H). HPLC (max plot) 99.9%; Rt 1.03 min. UPLC/MS: (MS+) 189.0 ([M+H]+).

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was triturated in EtOH
  3. filtrationthe precipitate filtered off
  4. customdried

Sources & evidence

ORD record
ord-9845cfb1be5f418390dfe81dc6eb2b01
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

Loading…