HCID 86704023, compound → HCID 86704028, compound

HRID 1773934Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][CH:9]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[CH2:16][CH2:15][N:14]3[C:10]2=[N:11][C:12]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:13]3[CH2:23][OH:24])[CH2:4][CH2:3]1>O1CCOCC1.O=[Mn]=O>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][CH:9]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[CH2:16][CH2:15][N:14]3[C:10]2=[N:11][C:12]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[C:13]3[CH:23]=[O:24])[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of [4-(1-methylpiperidin-4-yloxy)-2-phenyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulen-1-yl]-methanol (example 257A) (300 mg, 0.745 mmole) in 1,4-dioxane (4 mL) is added MnO2 (320 mg, 3.72 mmole) and the reaction mixture is heated at 90° C. overnight. Another portion of MnO2 (320 mg, 3.72 mmole) is added and the reaction mixture is heated at 90° C. overnight. The reaction mixture is filtered onto celite, cake washed with AcOEt and the solvent is removed under reduced pressure. The residue is purified by silica gel chromatography eluting with (CH2Cl2:MeOH) (100:0) to (95:5) to give 4-(1-methylpiperidin-4-yloxy)-2-phenyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene-1-carbaldehyde melting at 70° C.

Workup

temperaturethe reaction mixture is heated at 90° C. overnight
filtrationThe reaction mixture is filtered onto celite, cake
washwashed with AcOEt
customthe solvent is removed under reduced pressure
customThe residue is purified by silica gel chromatography
washeluting with (CH2Cl2:MeOH) (100:0) to (95:5)

Sources & evidence

ORD record: ord-eef4a67a42be40dcb8de646179a2fd35
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255101B2

Reaction notes

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