HCID 178487808, compound → HCID 178487807, compound

HRID 2273266Notes

Reaction equation

[C:1]([O:5][C:6](=[O:37])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([C:14]2[CH2:15][N:16](CC3C=CC=CC=3)[C:17]3[CH:18]=[N:19][C:20]4[C:25]([C:26]=3[CH:27]=2)=[N:24][C:23]([O:28][CH3:29])=[CH:22][CH:21]=4)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>[Pd].C(O)C>[C:1]([O:5][C:6](=[O:37])[NH:7][C@H:8]1[CH2:9][CH2:10][C@H:11]([CH:14]2[CH2:27][C:26]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([O:28][CH3:29])[N:24]=4)[N:19]=[CH:18][C:17]=3[NH:16][CH2:15]2)[CH2:12][CH2:13]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

10% Palladium on activated carbon (1.20 g, 1.13 mmol, 0.94 eq) is added at room temperature to a stirred solution of [trans-4-(1-benzyl-6-methoxy-1,2-dihydro-1,5,9-triaza-phenanthren-3-yl)-cyclohexyl]-carbamic acid tert-butyl ester (600 mg, 1.20 mmol, 1.0 eq) in ethanol (60 mL). The resulting mixture is stirred under hydrogen flow (1 bar) at 60° C. for 3 hours. The catalyst is then removed by filtration and the solution is concentrated to give the crude product that is purified by column chromatography (silica gel, eluent: petroleum ether:ethyl acetate: dichloromethane, 1:3:1, v/v/v) to afford [trans-4-(6-methoxy-1,2,3,4-tetrahydro-1,5,9-triaza-phenanthren-3-yl)-cyclohexyl]-carbamic acid tert-butyl ester as an off-white solid (292 mg, 59% yield).

Workup

customThe catalyst is then removed by filtration
concentrationthe solution is concentrated
customto give the crude product that
customis purified by column chromatography (silica gel, eluent: petroleum ether:ethyl acetate: dichloromethane, 1:3:1, v/v/v)

Sources & evidence

ORD record: ord-64ebb775b53249f7868018caa3c616cd
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120822B2

Reaction notes

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