Hydrochloric Acid → HCID 122512284, compound

HRID 1479042Notes

Reaction equation

HRID 1479042 reaction equation
C(OC([N:8]1[CH2:15][C:14]2[C:13]([NH2:16])=[N:12][NH:11][C:10]=2[C:9]1([CH3:18])[CH3:17])=O)(C)(C)C.[Cl:19][CH:20]([C:24](=O)[CH3:25])[C:21](=O)[CH3:22].Cl>CC(O)=O>[ClH:19].[Cl:19][C:20]1[C:24]([CH3:25])=[N:16][C:13]2[N:12]([N:11]=[C:10]3[C:9]([CH3:17])([CH3:18])[NH:8][CH2:15][C:14]3=2)[C:21]=1[CH3:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 743283-Chloro-2,4-pentanedioneHCID 40152088tert-Butyl 3-amino-6,6-dimethyl-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate

Product 1

HCID 122512284HCID 122512284, compoundYield 136.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3-amino-6,6-dimethyl-4,6-dihydro-1H-pyrrolo[3,4-c]pyrazole-5-carboxylic acid tert-butyl ester (500 mg; 1.98 mmol; 1 eq.) and 3-chloro-pentane-2,4-dione (226 μL; 1.98 mmol; 1.00 eq.) in AcOH (1.5 mL) was stirred at room temperature for 1 hour whereupon 32% aq. HCl (584 μL; 5.94 mmol; 3 eq.) was added. The resulting mixture was stirred for 4 hours then poured onto iPrOH (6 mL). The formed precipitate was filtered off and dried to afford the title compound (388 mg, 68%) as an off-white solid. 1H NMR (DMSO-d6) δ 10.37 (brs, 2H), 4.59 (s, 2H), 2.83 (s, 3H), 2.62 (s, 3H), 1.74 (s, 6H). HPLC (max plot) 98.1%, Rt 1.97 min. UPLC/MS: (MS+) 234.1 ([M+H]+).

Workup

  1. additionwas added
  2. additionthen poured onto iPrOH (6 mL)
  3. filtrationThe formed precipitate was filtered off
  4. customdried

Sources & evidence

ORD record
ord-d4f95b9f4d8a4d3e85c4159a730dd6d0
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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