Potassium Carbonate → HCID 22235448, compound

HRID 1743717Notes

Reaction equation

[CH:1]12[N:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:5]([CH2:6][CH2:7]1)[CH2:4][NH:3][CH2:2]2.C([O-])([O-])=O.[K+].[K+].CS(O[CH2:27][CH2:28][CH2:29][CH:30]([C:42]1[CH:47]=[CH:46][C:45]([C:48]#[N:49])=[CH:44][CH:43]=1)[O:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[C:34]([O:40][CH3:41])[CH:33]=1)(=O)=O>CN(C=O)C>[C:48]([C:45]1[CH:44]=[CH:43][C:42]([CH:30]([O:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[C:34]([O:40][CH3:41])[CH:33]=2)[CH2:29][CH2:28][CH2:27][N:3]2[CH2:4][CH:5]3[N:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:1]([CH2:7][CH2:6]3)[CH2:2]2)=[CH:47][CH:46]=1)#[N:49]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of tert-butyl 3,8-diazabicyclo[3.2.1]octane-8-carboxylate (7.1 g, 33.4 mmol; from Preparation B above) in DMF (120 mL) was added K2CO3 (5.1 g, 36.8 mmol) and 4-(4-cyanophenyl)-4-(3,4-dimethoxyphenoxy)butyl methanesulfonate (13.9 g, 34.4 mmol; see Preparation E, step (c) above). The resulting solution was heated to 90° C., stirred 4 h, cooled and concentrated in vacuo. The residue was suspended in H2O and extracted with CH2Cl2 (3×). The combined organics were dried (Na2SO4), filtered and concentrated in vacuo. Flash chromatography on silica gel eluting with CH2Cl2:MeOH (98:2) gave 17.3 g (99%) of the title compound.

Workup

temperaturecooled
concentrationconcentrated in vacuo
extractionextracted with CH2Cl2 (3×)
dry with materialThe combined organics were dried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-94e29a1ba5ca43d1a59a97058556b063
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07012074B2

Reaction notes

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