Lithium Hydroxide → HCID 69928688, compound

HRID 77401Notes

Reaction equation

[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:19][CH:18]3[CH:14]([CH2:15][N:16]([CH3:20])[CH2:17]3)[CH2:13]2)=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5].[OH-].[Li+].[CH2:23](OC(OCC)OCC)C>CO>[CH3:7][N:6]1[C:4](=[O:5])[C:3]2[C:2](=[CH:11][CH:10]=[C:9]([N:12]3[CH2:13][CH:14]4[CH:18]([CH2:17][N:16]([CH3:20])[CH2:15]4)[CH2:19]3)[CH:8]=2)[N:1]=[CH:23]1

Participants

Conditions

Temperature: 160 °C

Procedure

2-Amino-N-methyl-5-(5-methylhexahydropyrrolo[3,4-c]pyrrole-2(1H)-yl)benzamide (Intermediate 8A) (100 mg, 0.36 mmol) was dissolved in triethoxymethane (1 mL) and sealed in a microwave vial. Heated at 160° C. for 10 minutes. Reaction allowed to cool to room temperature and lithium hydroxide solution added (0.5 mL, 1M in methanol) and reaction stirred overnight. Organic layer loaded onto a 1 g SCX cartridge. The crude material was purified by SCX, and the solvent removed under reduced pressure. The crude material was then re-dissolved in methanol (1 mL) and purified by preparative-HPLC. Purified sample was free-based using 500 mg SCX cartridge to afford 3-methyl-6-(5-methylhexahydropyrrolo[3,4-c]pyrrole-2(1H)-yl)quinazolin-4(3H)-one (56 mg, 0.2 mmol).

Workup

customsealed in a microwave vial
customReaction
temperatureto cool to room temperature
customThe crude material was purified by SCX
customthe solvent removed under reduced pressure
dissolutionThe crude material was then re-dissolved in methanol (1 mL)
custompurified by preparative-HPLC
customPurified sample

Sources & evidence

ORD record: ord-7d2bf6bfb9384f03b91ce19946d24598
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841289B2

Reaction notes

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