Diethyl 2-fluoro-2-methyl-3-oxobutanedioate → HCID 178471754, compound

HRID 2278842Notes

Reaction equation

HRID 2278842 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14](=[NH:17])[NH:15][NH2:16])=[N:6]1.[F:22][C:23]([CH3:36])([C:29](=O)[C:30](OCC)=[O:31])[C:24]([O:26][CH2:27][CH3:28])=[O:25]>C(O)C>[F:22][C:23]([C:29]1[N:16]=[N:15][C:14]([C:7]2[C:8]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[N:5]([CH2:4][C:3]3[CH:18]=[CH:19][CH:20]=[CH:21][C:2]=3[F:1])[N:6]=2)=[N:17][C:30]=1[OH:31])([CH3:36])[C:24]([O:26][CH2:27][CH3:28])=[O:25]

Participants

4

Reactant 2

HCID 89689509Diethyl 2-fluoro-2-methyl-3-oxobutanedioateHCID 178512735HCID 178512735, compound

Product 1

HCID 178471754HCID 178471754, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.000 g (purity 67%, approx. 2.357 mmol) of 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidohydrazide in 15 ml of absolute ethanol were initially introduced and admixed with 1.557 g (7.070 mmol) of diethyl 2-fluoro-2-methyl-3-oxobutanedioate (described in J. Med. Chem. 1966, 9, 149-151). The mixture was stirred at RT overnight and then concentrated. The residue was purified by preparative HPLC (mobile phase: methanol/water, gradient 30:70→95:5). This gave 230 mg of the target compound (purity 95%; 21% of theory).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by preparative HPLC (mobile phase: methanol/water, gradient 30:70→95:5)

Sources & evidence

ORD record
ord-c920d9fddf01476fa1e9c6dd552a2d68
Source dataset
uspto-grants-2015_09
Patent number
US09133191B2

Reaction notes

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