Potassium Carbonate → HCID 67319418, compound

HRID 1807586Notes

Reaction equation

HRID 1807586 reaction equation
Cl.[NH2:2][C@@H:3]1[CH2:12][CH2:11][CH2:10][C:9]2[C:8]([C:13]3[N:17]=[C:16]([C:18]4[CH:19]=[CH:20][C:21]([O:26][CH:27]([CH3:29])[CH3:28])=[C:22]([CH:25]=4)[C:23]#[N:24])[O:15][N:14]=3)=[CH:7][CH:6]=[CH:5][C:4]1=2.Br[CH2:31][C:32]([O:34][CH3:35])=[O:33].C([O-])([O-])=O.[K+].[K+]>CC#N.[Cl-].[Na+].O>[C:23]([C:22]1[CH:25]=[C:18]([C:16]2[O:15][N:14]=[C:13]([C:8]3[CH:7]=[CH:6][CH:5]=[C:4]4[C:9]=3[CH2:10][CH2:11][CH2:12][C@H:3]4[NH:2][CH2:31][C:32]([O:34][CH3:35])=[O:33])[N:17]=2)[CH:19]=[CH:20][C:21]=1[O:26][CH:27]([CH3:29])[CH3:28])#[N:24]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 67198744HCID 67198744, compound

Product 1

HCID 67319418HCID 67319418, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirring solution of (R)-5-(3-(5-amino-5,6,7,8-tetrahydronaphthalen-1-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile 3 (119 mg, 0.32 mmol) in CH3CN (5.0 mL) was added methyl bromoacetate (53.5 μL, 0.35 mmol) and K2CO3 (138 mg, 1.27 mmol). After stirring for 18 h, the mixture was diluted with brine and washed with NaHCO3. The organic layer was dried with Na2SO4 and concentrated. The resulting crude solid was purified by chromatography (MeOH/DCM) to provide 113.1 mg (79%) of (R)-methyl 2-((5-(5-(3-cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-1,2,3,4-tetrahydronaphthalen-1-yl)amino)acetate INT-18. LCMS-ESI (m/z) calculated for C25H26N4O4: 446.5; found 447.2 [M+H]+, tR=2.52 min.

Workup

  1. washwashed with NaHCO3
  2. dry with materialThe organic layer was dried with Na2SO4
  3. concentrationconcentrated
  4. customThe resulting crude solid was purified by chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-83e5df096f0e4d328599d8007eb6cb17
Source dataset
uspto-grants-2013_01
Patent number
US08357706B2

Reaction notes

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