4-tert-Butylcyclohexylamine → HCID 178445674, compound

HRID 1072548Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[N:4][N:3]=1.[C:19]([CH:23]1[CH2:28][CH2:27][CH:26]([NH2:29])[CH2:25][CH2:24]1)([CH3:22])([CH3:21])[CH3:20].C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[C:19]([C@@H:23]1[CH2:24][CH2:25][C@H:26]([NH:29][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([CH2:12][C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[N:4][N:3]=2)[CH2:27][CH2:28]1)([CH3:22])([CH3:20])[CH3:21]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 1.0 g (3.91 mmol) 1-chloro-4-(4-pyridylmethyl)phthalazine (Example 67.A1 in WO 98/35958) and 1.82 g (11.7 mmol) 4-tert-butylcyclohexylamine (trans-/cis-mixture) is stirred overnight at 120° C. The cooled reaction mixture is then distributed between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic phase is washed with water and brine, dried (MgSO4) and evaporated and the residue purified on silica gel by flash chromatography using dichloromethane/methanol (9:1) yielding the title compound as a trans-/cis-mixture: FAB MS (M+H)+=375. Separation of the isomers by reversed phase medium pressure chromatography (CH3CN/H2O/trace of TFA) gives the cis-isomer (m.p. 64-65° C.) followed by the trans-isomer (m.p. 132-134° C.).

Workup

customThe cooled reaction mixture
washThe organic phase is washed with water and brine
dry with materialdried (MgSO4)
customevaporated
customthe residue purified on silica gel by flash chromatography

Sources & evidence

ORD record: ord-b1f8468813ed438aa65235850526a4df
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06911440B2

Reaction notes

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