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

HRID 1478993Notes

Reaction equation

HRID 1478993 reaction equation
[ClH:1].C(OC([N:9]1[CH2:21][C:12]2=[C:13]3[N:18]([N:19]=[C:11]2[CH2:10]1)[CH:17]=[C:16]([CH3:20])[CH:15]=[N:14]3)=O)(C)(C)C.CCO>CC(O)=O>[ClH:1].[CH3:20][C:16]1[CH:15]=[N:14][C:13]2[N:18]([N:19]=[C:11]3[CH2:10][NH:9][CH2:21][C:12]3=2)[CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 896439646-methyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carboxylic acid tert-butyl ester

Product 1

HCID 896439966-methyl-2,3-dihydro-1H-2,4,7a,8-tetraaza-cyclopenta[a]indene hydrochlorideYield 65.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Aq. 32% HCl (1.61 mL; 16.4 mmol; 3 eq.) was added to a solution of 6-methyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carboxylic acid tert-butyl ester (1.5 g; 5.47 mmol; 1 eq.) in AcOH (7.5 mL) and the resulting mixture was stirred at room temperature for 28 hours then poured dropwise into EtOH (40 mL) under vigorous stirring. The precipitate was filtered off, washed with EtOH then MTBE and dried to afford the title compound (0.75 g, 65%) as a white solid. 1H NMR (DMSO-d6) δ 10.50 (s, 2H), 9.06-9.02 (m, 1H), 8.51 (d, J=2.1 Hz, 1H), 4.55-4.52 (m, 4H), 2.33 (s, 3H). HPLC (max plot) 100.0%; Rt 4.36 min.

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with EtOH
  3. dry with materialMTBE and dried

Sources & evidence

ORD record
ord-3ab7049e4fa34260b7bb5a984749ac87
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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