HCID 67350115, compound → HCID 67352803, compound

HRID 1672809Notes

Reaction equation

HRID 1672809 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>CC1OCCN=1>[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]([CH2:12][CH2:13][NH:14][C:15](=[O:16])[CH3:6])[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

3

Reactant 1

HCID 67350115HCID 67350115, compound

Product 1

HCID 67352803HCID 67352803, compoundYield 268.3%

Reagents, catalysts & solvents 1

HCID 707132-Methyl-2-oxazolineSolvent

Conditions

Temperature
100 °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 (140 mg, 0.34 mmol) obtained in Step 1 of Example 89 was suspended in 2-methyl-2-oxazoline (1.0 mL), and the mixture was stirred overnight at 100° C. The residue obtained by concentrating the mixture under reduced pressure was then purified by silica gel column chromatography to give (S)—N-(2-{5-[3-(9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)phenyl]-2-oxo-1,3,4-oxadiazol-3(2H)-yl}ethyl)acetamide (226 mg, quantitative).

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-6456696cb40b4032989d69bf53710533
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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