Pyruvic Acid → HCID 118275230, compound

HRID 526015Notes

Reaction equation

[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=O.N12CCN(CC1)CC2.[NH2:15][C:16]1[N:21]=[C:20]([CH3:22])[C:19]([CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:18][C:17]=1I>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:27]([O:26][C:25]([NH:24][CH2:23][C:19]1[CH:18]=[C:17]2[CH:4]=[C:2]([C:1]([OH:6])=[O:5])[NH:15][C:16]2=[N:21][C:20]=1[CH3:22])=[O:31])([CH3:30])([CH3:29])[CH3:28]

Participants

Conditions

Temperature: 100 °C

Procedure

Under argon, pyruvic acid (6.90 ml, 100.1 mmol) and 1,4-diazabicyclo[2.2.2]octane (843 g, 7.51 mmol) were added to a solution of tert-butyl [(6-amino-5-iodo-2-methylpyridin-3-yl)methyl]carbamate (840 mg, 2.31 mmol) in N,N-dimethylformamide (0.5 ml), and the flask was evacuated and flushed with argon. Then argon was passed through the solution for 5 min and then palladium(II) acetate (25.9 mg, 0.11 mmol) was added and the mixture was heated to 100° C. for 2 h. The cooled solution was filtered through Celite and the dimethylformamide was distilled off. The residue was then taken up in water and acidified with hydrochloric acid, giving a 5-{[(tert-butoxycarbonyl)amino]methyl}-6-methyl-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid (650 g, 88% of theory). HPLC-MS: log P=0.58; mass (m/z): 306.1 (M+H)+; 1H-NMR (DMSO) 1.37 (s, 9H), 2.33 (s, 3H), 4.17 (d, 2H), 6.57 (s, 1H), 7.68 (s, 1H).

Workup

customthe flask was evacuated
customflushed with argon
filtrationThe cooled solution was filtered through Celite
distillationthe dimethylformamide was distilled off

Sources & evidence

ORD record: ord-c4f29563ee354cd49113700042663cd5
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09345247B2

Reaction notes

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