Chloroform → HCID 67349193, compound

HRID 1672830Notes

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:24][CH:25]=[C:26]([C:28]([NH2:30])=O)[N:27]=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:31]=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.C(Cl)(Cl)Cl>N1C=CC=CC=1>[C:28]([C:26]1[N:27]=[C:23]([C:19]2[CH:18]=[C:17]([N:14]3[CH2:13][C@H:12]4[N:8]([CH2:9][CH2:10][CH2:11]4)[C:7]4[N:31]=[C:3]([S:2][CH3:1])[N:4]=[CH:5][C:6]=4[C:15]3=[O:16])[CH:22]=[CH:21][CH:20]=2)[O:24][CH:25]=1)#[N:30]

Participants

Conditions

Temperature: 90 °C

Procedure

(S)-2-[3-(9-Methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)phenyl]-1,3-oxazole-4-carboxamide (211 mg, 0.483 mmol) obtained in Step 1 was dissolved in pyridine (3 mL), and the mixture was stirred at 90° C. for 3.5 hours after adding p-toluenesulfonyl chloride (395 mg, 2.07 mmol). The mixture was diluted by addition of chloroform, and washed with 1 mol/L hydrochloric acid and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the residue obtained upon concentration under reduced pressure was then purified by silica gel column chromatography to give (S)-5-[3-(4-cyano-1,3-oxazol-2-yl)phenyl]-9-methylthio-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (155 mg, 77%).

Workup

washwashed with 1 mol/L hydrochloric acid and saturated brine
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
customthe residue obtained upon concentration under reduced pressure
customwas then purified by silica gel column chromatography

Sources & evidence

ORD record: ord-e7f0991fefb443d28ac50a6e85442001
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998954B2

Reaction notes

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