Potassium Carbonate → HCID 58344804, compound

HRID 1809529Notes

Reaction equation

HRID 1809529 reaction equation
C([O:4][CH2:5][CH2:6][N:7]([C@H:12]1[C:20]2[C:15](=[C:16]([C:21]3[N:25]=[C:24]([C:26]4[CH:31]=[CH:30][C:29]([O:32][CH:33]([CH3:35])[CH3:34])=[C:28]([C:36]#[N:37])[CH:27]=4)[O:23][N:22]=3)[CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13]1)[S:8]([CH3:11])(=[O:10])=[O:9])(=O)C.C([O-])([O-])=O.[K+].[K+]>CO.O>[C:36]([C:28]1[CH:27]=[C:26]([C:24]2[O:23][N:22]=[C:21]([C:16]3[CH:17]=[CH:18][CH:19]=[C:20]4[C:15]=3[CH2:14][CH2:13][C@H:12]4[N:7]([CH2:6][CH2:5][OH:4])[S:8]([CH3:11])(=[O:9])=[O:10])[N:25]=2)[CH:31]=[CH:30][C:29]=1[O:32][CH:33]([CH3:35])[CH3:34])#[N:37]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 131730181HCID 131730181, compound

Product 1

HCID 58344804HCID 58344804, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of (R)-2-(N-(4-(5-(3-cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-yl)methylsulfonamido)ethyl acetate (12 mg, 0.22 mmol) in a 1:1 mixture of MeOH/H2O was added K2CO3 (9.48 mg, 0.06 mmol). The reaction mixture was stirred at room temperature for 2 h and concentrated to dryness. The crude reaction mixture purified by preparative HPLC to afford (R)—N-(4-(5-(3-cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-yl)-N-(2-hydroxyethyl)methanesulfonamide 112. LCMS-ESI (m/z) calculated for C24H26N4O5S: 482.2; found 505.1 [M+Na]+, tR=3.55 min.

Workup

  1. concentrationconcentrated to dryness
  2. customThe crude reaction mixture
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-7fbbe6d47d624842b282899cce98395f
Source dataset
uspto-grants-2013_01
Patent number
US08362048B2

Reaction notes

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