Dichloromethane → HCID 67421401, compound

HRID 1987323Notes

Reaction equation

[CH:1]([C:4]1[C:5]([CH:10]2[CH2:15][C:14](=O)[CH2:13][CH:12]([C:17]3[C:22]([CH:23]([CH3:25])[CH3:24])=[CH:21][CH:20]=[CH:19][N:18]=3)[NH:11]2)=[N:6][CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2].[OH-].[K+].O.NN.C(Cl)Cl>C(O)COCCO>[CH:1]([C:4]1[C:5]([C@H:10]2[CH2:15][CH2:14][CH2:13][C@@H:12]([C:17]3[C:22]([CH:23]([CH3:25])[CH3:24])=[CH:21][CH:20]=[CH:19][N:18]=3)[NH:11]2)=[N:6][CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 3,3″-diisopropyl-2′,3′,5′,6′-tetrahydro-1′H-[2,2′;6′,2″]terpyridin-4′-one (106 mg, 0.314 mmol) in diethylene glycol (3 mL) were added KOH (352 mg, 6.29 mmol) and hydrazine monohydrate (0.61 mL, 12.6 mmol). The reaction mixture was heated to ˜100° C. for 1 h using a sand bath. After 1 h the temperature was raised to 200° C. for about 45 minutes. CH2Cl2 (50 mL) was added to the remaining mixture and was washed with water (3 times 50 mL). The organic layer was dried (MgSO4), filtered and concentrated to provide 100 mg (99%) of 3,3″-diisopropyl-1′,2′,3′,4′,5′,6′-hexahydro-cis-[2,2′;6′,2″]terpyridine (with some DEG). 1H NMR(CDCl3) δ 1.25 (d, 6H, J=9.3 Hz), 1.57-1.65 (m, 2H), 1.68-1.89 (m, 3H), 2.10-2.14 (m, 1H), 3.19-3.30 (m, 3H), 4.33 (br s, 1H), 7.10 (dd, 2H, J=7.8, 4.5 Hz), 7.53 (d, 2H, J=7.8 Hz), 8.46 (d, 2H, J=4.5 Hz).

Workup

temperatureAfter 1 h the temperature was raised to 200° C. for about 45 minutes
washwas washed with water (3 times 50 mL)
dry with materialThe organic layer was dried (MgSO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-7afaf5d89ad44bee9f38846f5983077f
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07550484B2

Reaction notes

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