Diethyl bromomalonate → HCID 178470551, compound

HRID 869191Notes

Reaction equation

HRID 869191 reaction equation
[C:1]([C:4]1[N:9]=[N:8][C:7]([N:10]([CH2:18][C:19]2([C:23]3[C:28]([F:29])=[CH:27][CH:26]=[CH:25][N:24]=3)[CH2:22][CH2:21][CH2:20]2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:6][CH:5]=1)(=[S:3])[NH2:2].[CH2:30]([O:32][C:33](=[O:41])[CH:34](Br)[C:35](OCC)=[O:36])[CH3:31]>C1(C)C=CC=CC=1>[C:13]([O:12][C:11]([N:10]([CH2:18][C:19]1([C:23]2[C:28]([F:29])=[CH:27][CH:26]=[CH:25][N:24]=2)[CH2:22][CH2:21][CH2:20]1)[C:7]1[N:8]=[N:9][C:4]([CH:1]2[N:2]=[C:35]([OH:36])[CH:34]([C:33]([O:32][CH2:30][CH3:31])=[O:41])[S:3]2)=[CH:5][CH:6]=1)=[O:17])([CH3:16])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 69637Diethyl bromomalonateHCID 86686139HCID 86686139, compound

Product 1

HCID 178470551HCID 178470551, compoundYield 17.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

t-Butyl 6-carbamothioylpyridazin-3-yl((1-(3-fluoropyridin-2-yl)cyclobutyl)methyl)carbamate (1.0 g, 2.4 mmol), diethylbromomalonate (2 mL, 12 mmol), and toluene were added to a round bottom flask, heated to 90° C., and stirred for 40 min. The reaction was concentrated and purified using reverse phase chromatography to yield 219 mg of ethyl 2-(6-(t-butoxycarbonyl((1-(3-fluoropyridin-2-yl)cyclobutyl)methyl)amino)pyridazin-3-yl)-4-hydroxy-2,5-dihydrothiazole-5-carboxylate as an off-white solid.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified

Sources & evidence

ORD record
ord-b32a9b7c85b1460d8e6575cf8e3d3965
Source dataset
uspto-grants-2015_03
Patent number
US08969346B2

Reaction notes

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