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

HRID 1478998Notes

Reaction equation

HRID 1478998 reaction equation
[ClH:1].O1CCOCC1.C(OC([N:15]1[CH2:27][C:18]2=[C:19]3[N:24]([N:25]=[C:17]2[CH2:16]1)[CH:23]=[C:22]([Br:26])[CH:21]=[N:20]3)=O)(C)(C)C>>[ClH:1].[Br:26][C:22]1[CH:21]=[N:20][C:19]2[N:24]([N:25]=[C:17]3[CH2:16][NH:15][CH2:27][C:18]3=2)[CH:23]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 896439276-bromo-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carboxylic acid tert-butyl ester

Product 1

HCID 896439756-bromo-2,3-dihydro-1H-2,4,7a,8-tetraaza-cyclopenta[a]indene hydrochlorideYield 96%

Procedure

A 4M solution of HCl in 1,4-dioxane (35 mL; 140 mmol; 23.7 eq.) was added to 6-bromo-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carboxylic acid tert-butyl ester (2 g; 5.9 mmol; 1 eq.) and the resulting mixture was stirred at room temperature for 18 hours. The precipitate was filtered off, washed with Et2O and dried to afford the title compound (1.56 g, 96%) as beige solid. 1H NMR (DMSO-d6) δ 10.61 (br s, 2H), 9.68 (d, J=2.2 Hz, 1H), 8.69 (d, J=2.2 Hz, 1H), 4.56 (s, 4H). UPLC/MS: (MS+) 239.1 and 241.1 ([M+H]+).

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with Et2O
  3. customdried

Sources & evidence

ORD record
ord-8f3e4a9ab1eb4329ac41be83f90b1939
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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