2-Bromopropanedial → 6-bromo-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carboxylic acid tert-butyl ester

HRID 1478997Notes

Reaction equation

HRID 1478997 reaction equation
[Br:1][CH:2]([CH:5]=O)[CH:3]=O.[C:7]([O:11][C:12]([N:14]1[CH2:21][C:20]2[C:16](=[N:17][NH:18][C:19]=2[NH2:22])[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>CC(O)=O>[C:7]([O:11][C:12]([N:14]1[CH2:21][C:20]2=[C:19]3[N:18]([N:17]=[C:16]2[CH2:15]1)[CH:3]=[C:2]([Br:1])[CH:5]=[N:22]3)=[O:13])([CH3:10])([CH3:8])[CH3:9]

Participants

4

Reactant 2

HCID 749452-BromopropanedialHCID 178451527HCID 178451527, compound

Product 1

HCID 896439276-bromo-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carboxylic acid tert-butyl esterYield 45%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of bromomalonaldehyde (2.02 g; 13.38 mmol; 1 eq.) and 3-amino-2,6-dihydro-4H-pyrrolo[3,4-c]pyrazole-5-carboxylic acid tert-butyl ester (3 g; 13.38 mmol; 1 eq.) in AcOH (21 mL) was stirred at room temperature for 40 minutes. The insoluble material was removed by filtration and the solution diluted with water (60 mL). The precipitate was filtered off, washed with water (3×) and dried. Recrystallization from iPrOH afforded the title compound (2.02 g, 45%) as beige solid. 1H NMR (DMSO-d6) δ 9.60 (d, J=2.2 Hz, 1H), 8.60 (d, J=2.2 Hz, 1H), 4.62-4.55 (m, 4H), 1.47 (s, 9H). HPLC (max plot) 99.8%; Rt 3.54 min. UPLC/MS: (MS+) 339.3 and 341.3 ([M+H]+).

Workup

  1. customThe insoluble material was removed by filtration
  2. additionthe solution diluted with water (60 mL)
  3. filtrationThe precipitate was filtered off
  4. washwashed with water (3×)
  5. customdried
  6. customRecrystallization from iPrOH

Sources & evidence

ORD record
ord-1d8e5928843c4263ac9c6d2950ce7b69
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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