Acetic Acid → 6-chloro-5,7-dimethyl-2,3-dihydro-1H-2,4,7a,8-tetraaza-cyclopenta[a]indene hydrochloride

HRID 1478989Notes

Reaction equation

HRID 1478989 reaction equation
C(OC([N:8]1[CH2:15][C:14]2[C:10](=[N:11][NH:12][C:13]=2[NH2:16])[CH2:9]1)=O)(C)(C)C.[Cl:17][CH2:18][C:19]([CH2:21]C(=O)C)=O.O.[CH3:26][C:27](O)=O>>[ClH:17].[Cl:17][C:18]1[C:19]([CH3:21])=[N:16][C:13]2[N:12]([N:11]=[C:10]3[CH2:9][NH:8][CH2:15][C:14]3=2)[C:27]=1[CH3:26]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 144968561-Chloro-2,4-pentanedioneHCID 178451527HCID 178451527, compound

Product 1

HCID 896439086-chloro-5,7-dimethyl-2,3-dihydro-1H-2,4,7a,8-tetraaza-cyclopenta[a]indene hydrochlorideYield 90%

Procedure

A solution of 3-amino-2,6-dihydro-4H-pyrrolo[3,4-c]pyrazole-5-carboxylic acid tert-butyl ester (1 g; 4.46 mmol; 1 eq.) and 3-chloroacetylacetone (0.71 mL; 6.24 mmol; 1.4 eq.) in AcOH (10 mL) was stirred at room temperature for 18 hours. The reaction was poured into water (100 mL) under vigorous stirring and the precipitate filtered off, washed with water (3×) and dried to afford the title compound (1298 mg, 90%) as an off-white solid. 1H NMR (DMSO-d6) δ 4.60-4.52 (m, 4H), 2.81 (br s, 3H), 2.60-2.57 (m, 3H), 1.48 (s, 9H). HPLC (max plot) 98.4%; Rt 3.96 min. UPLC/MS: (MS+) 323 ([M+H]+).

Workup

  1. filtrationthe precipitate filtered off
  2. washwashed with water (3×)
  3. customdried

Sources & evidence

ORD record
ord-2e8f2f7edd824b4189ec9060af9e0218
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

Loading…