Methanol → (S)-4-methyl-3-[3-(9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)phenyl]-1,2,4-oxadiazol-5(4H)-one

HRID 1672807Notes

Reaction equation

HRID 1672807 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[NH:27][C:26](=[O:28])[O: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.CO.[C:32]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:32][N:27]1[C:26](=[O:28])[O:25][N:24]=[C:23]1[C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([N:14]2[CH2:13][C@H:12]3[N:8]([CH2:9][CH2:10][CH2:11]3)[C:7]3[N:29]=[C:3]([S:2][CH3:1])[N:4]=[CH:5][C:6]=3[C:15]2=[O:16])[CH:18]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 136337081(S)-3-[3-(9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)phenyl]-1,2,4-oxadiazol-5(4H)-one

Product 1

HCID 67351506(S)-4-methyl-3-[3-(9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)phenyl]-1,2,4-oxadiazol-5(4H)-oneYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-3-[3-(9-Methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)phenyl]-1,2,4-oxadiazol-5(4H)-one (150 mg, 0.37 mmol) obtained in Step 1 was suspended in THF (2.0 mL), and the mixture was stirred at room temperature for 2 hours after adding methanol (0.022 mL, 0.55 mmol), triphenylphosphine (144 mg, 0.55 mmol), and diethyl azodicarboxylate (40% toluene solution, 0.25 mL, 0.55 mmol). The residue obtained by concentrating the mixture under reduced pressure was then purified by silica gel column chromatography to give (S)-4-methyl-3-[3-(9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)phenyl]-1,2,4-oxadiazol-5(4H)-one (127 mg, 82%).

Workup

  1. customThe residue obtained
  2. concentrationby concentrating the mixture under reduced pressure
  3. customwas then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9760a05adcb74b109ef0512b2eb0746f
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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