Ethyl bromopyruvate → HCID 136414064, compound

HRID 336858Notes

Reaction equation

HRID 336858 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:19]([NH:20][C:21]([SH:23])=[NH:22])=[N:18][NH:17][C:6]2=[N:7][C:8]=1[C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[F:16])#[N:2].Br[CH2:25][C:26](=O)[C:27]([O:29][CH2:30][CH3:31])=[O:28]>C(O)C>[C:1]([C:3]1[CH:4]=[C:5]2[C:19]([NH:20][C:21]3[S:23][CH:25]=[C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:22]=3)=[N:18][NH:17][C:6]2=[N:7][C:8]=1[C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[F:16])#[N:2]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 178509419HCID 178509419, compound

Product 1

HCID 136414064HCID 136414064, compoundYield 44.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 66 mg (0.20 mmol) of N-(5-cyano-6-(2-fluoro-4-hydroxyphenyl)-1H-pyrazolo[3,4-b]pyridine-3-yl)carbamimidothioic acid diluted in 2 ml of ethanol are added 57 mg (0.20 mmol, 68%) of ethyl 3-bromo-2-oxopropanoate. The solution is refluxed for 2 h. The solid is filtered, washed with ethanol and dried to give 38 mg of ethyl 2-(5-cyano-6-(2-fluoro-4-hydroxyphenyl)-1H-pyrazolo[3,4-b]pyridine-3-ylamino)thiazole-4-carboxylate in the form of a yellow solid.

Workup

  1. temperatureThe solution is refluxed for 2 h
  2. filtrationThe solid is filtered
  3. washwashed with ethanol
  4. customdried

Sources & evidence

ORD record
ord-e320e6afeab54707b0fd2e2591ae6dc4
Source dataset
uspto-grants-2014_11
Patent number
US08889711B2

Reaction notes

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