HCID 12721726, compound → HCID 89662793, compound

HRID 1479046Notes

Reaction equation

HRID 1479046 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][CH:18]([CH:22](OCC)OCC)[C:19](=O)[CH3:20]>CC(O)=O>[Cl:17][C:18]1[C:19]([CH3:20])=[N:16][C:13]2[N:12]([N:11]=[C:10]3[CH2:9][NH:8][CH2:15][C:14]3=2)[CH:22]=1

Participants

4

Reactant 2

HCID 12721726HCID 12721726, compoundHCID 178451527HCID 178451527, compound

Product 1

HCID 89662793HCID 89662793, compoundYield 31.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-amino-2,6-dihydro-4H-pyrrolo[3,4-c]pyrazole-5-carboxylic acid tert-butyl ester (5.8 g; 25.9 mmol; 1 eq.) and 3-chloro-4,4-diethoxy-butan-2-one (5.6 g; 25.9 mmol; 1 eq.) in AcOH (26 mL) was stirred at room temperature for 16 hours then concentrated in vacuo. The residue was poured onto sat. aq. NaHCO3 and the formed precipitate was filtered off and dried. Purification by column chromatography (30% EA in heptane) afforded the title compound (1.7 g, 22%) as a white solid. 1H NMR (DMSO-d6) δ 9.48 (s, 1H), 4.62-4.54 (m, 4H), 2.60-2.57 (m, 3H), 1.48 (s, 9H). HPLC (max plot) 97.0%, Rt 3.93 min. UPLC/MS: (MS+) 309.3 ([M+H]+).

Workup

  1. concentrationthen concentrated in vacuo
  2. additionThe residue was poured onto sat. aq. NaHCO3
  3. filtrationthe formed precipitate was filtered off
  4. customdried
  5. customPurification by column chromatography (30% EA in heptane)

Sources & evidence

ORD record
ord-04d8eba4c7d94cfdbd8180891b6dc24d
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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