Hydrochloric Acid → HCID 131736543, compound

HRID 1478996Notes

Reaction equation

HRID 1478996 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)[CH:23]=[C:22]([CH3:26])[C:21]([CH3:27])=[N:20]3)=O)(C)(C)C>CO>[ClH:1].[ClH:1].[CH3:27][C:21]1[C:22]([CH3:26])=[CH:23][N:24]2[C:19]([N:20]=1)=[C:18]1[CH2:28][NH:15][CH2:16][C:17]1=[N:25]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 89643935HCID 89643935, compound

Product 1

HCID 131736543HCID 131736543, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 4M solution of HCl in 1,4-dioxane (10 mL; 40 mmol; 67.8 eq.) was added to a solution of 5,6-dimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carboxylic acid tert-butyl ester (170 mg; 0.59 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 (90 mg, 58%) as a pale yellow solid. 1H NMR (DMSO-d6) δ 10.41 (br s, 2H), 8.66-8.17 (br s, 1H), 8.45 (s, 1H), 4.57-4.53 (m, 4H), 2.70 (s, 3H), 2.35 (s, 3H). HPLC (max plot) 99.6%; 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-b825529c034849888c9189626d1f63fa
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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