Water → HCID 67349075, compound

HRID 1672808Notes

Reaction equation

HRID 1672808 reaction equation
[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[C:15](=[O:16])[N:14]([C:17]3[CH:18]=[C:19]([C:23]4[O:27][C:26](=[O:28])[NH:25][N:24]=4)[CH:20]=[CH:21][CH:22]=3)[CH2:13][C@H:12]3[N:8]([CH2:9][CH2:10][CH2:11]3)[C:7]=2[N:29]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:37][C:38](=[O:40])[CH3:39].O>CN(C=O)C>[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[C:15](=[O:16])[N:14]([C:17]3[CH:18]=[C:19]([C:23]4[O:27][C:26](=[O:28])[N:25]([CH2:37][C:38](=[O:40])[CH3:39])[N:24]=4)[CH:20]=[CH:21][CH:22]=3)[CH2:13][C@H:12]3[N:8]([CH2:9][CH2:10][CH2:11]3)[C:7]=2[N:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 67350115HCID 67350115, compound

Product 1

HCID 67349075HCID 67349075, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-5-[3-(9-Methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)phenyl]-1,3,4-oxadiazol-2(3H)-one (140 mg, 0.34 mmol) obtained in Step 1 of Example 89 was dissolved in DMF (3.0 mL), and the mixture was stirred at room temperature for 1 hour after adding potassium carbonate (94 mg, 0.68 mmol) and chloroacetone (0.030 mL, 0.38 mmol). Thereafter, water was added to the mixture, and the precipitated pale yellow solid was filtered off to obtain (S)-5-[3-(9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)phenyl]-3-(2-oxopropyl)-1,3,4-oxadiazol-2(3H)-one (144 mg, 91%).

Workup

  1. filtrationthe precipitated pale yellow solid was filtered off

Sources & evidence

ORD record
ord-d4956ea2d45b4a718248668e0ebdb159
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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