Methanol → HCID 67350482, compound

HRID 1672805Notes

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.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:25]1[N:24]=[C:23]([C:19]2[CH:20]=[CH:21][CH:22]=[C:17]([N:14]3[CH2:13][C@H:12]4[N:8]([CH2:9][CH2:10][CH2:11]4)[C:7]4[N:29]=[C:3]([S:2][CH3:1])[N:4]=[CH:5][C:6]=4[C:15]3=[O:16])[CH:18]=2)[O:27][C:26]1=[O:28]

Participants

Conditions

Temperature: 55 °C

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 (280 mg, 0.68 mmol) obtained in Step 1 was suspended in THF (5.0 mL), and the mixture was stirred at 55° C. for 5 hours after adding methanol (0.082 mL, 2.04 mmol), triphenylphosphine-supported resin (Triphenylphosphine, polymer-supported; 3.08 mmol P/G, 1.02 g, 3.06 mmol), and diethyl azodicarboxylate (40% toluene solution, 0.92 mL, 2.04 mmol). The resin was separated by filtration, and the filtrate was collected, and concentrated under reduced pressure. The resulting residue was then purified by silica gel column chromatography to give (S)-3-methyl-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 (305 mg, quantitative).

Workup

customThe resin was separated by filtration
customthe filtrate was collected
concentrationconcentrated under reduced pressure
customThe resulting residue was then purified by silica gel column chromatography

Sources & evidence

ORD record: ord-3a1fe6bc968e43d7b2171f321dfe3fea
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998954B2

Reaction notes

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