Formic Acid → HCID 118079722, compound

HRID 1485758Notes

Reaction equation

[CH:1]([O-:3])=O.[Na+].C(O)=O.[O:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13]([N:15]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:25]3[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][CH:26]=3)[CH:23]=2)[NH:18][C@@H:17]([CH3:35])[CH2:16]1)=[O:14]>>[O:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13]([N:15]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:25]3[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:32])=[O:33])=[CH:27][CH:26]=3)[CH:23]=2)[N:18]([CH:1]=[O:3])[C@@H:17]([CH3:35])[CH2:16]1)=[O:14]

Participants

Reactant 3

HCID 284Formic Acid

HCID 2723810Sodium Formate

HCID 118079525HCID 118079525, compound

Product 1

HCID 118079722HCID 118079722, compoundYield 72%

Procedure

Sodium formate (14 mg, 0.200 mmol) and formic acid (46 mg, 1.0 mmol) were added to (S)-furan-2-yl(3-methyl-7-(4-(methylsulfonyl)phenyl)-3,4-dihydroquinoxaline-1(2H)-yl)methanone (0.2 M in 1,2-dichloroethane, 0.1 mL, 0.02 mmol) and shaken at room temperature for 5 h. The reaction was concentrated and the crude product was purified by mass-triggered preparatory HPLC. The product-containing fractions were combined and concentrated to afford (S)-4-(furan-2-carbonyl)-2-methyl-6-(4-(methylsulfonyl)phenyl)-3,4-dihydroquinoxaline-1(2H)-carbaldehyde (0.0061 g, 72%). MS (ESI, pos. ion) m/z 425.

Workup

concentrationThe reaction was concentrated
customthe crude product was purified by mass-triggered preparatory HPLC
concentrationconcentrated

Sources & evidence

ORD record: ord-6cb23fe86f414aa5ae9b006ef5e43711
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422281B2

Reaction notes

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