Potassium Carbonate → HCID 54119206, compound

HRID 1596478Notes

Reaction equation

[CH:1]1([CH2:4][OH:5])[CH2:3][CH2:2]1.C1N=CN([C:11]([N:13]2[CH:17]=N[CH:15]=[CH:14]2)=[O:12])C=1.[CH:18]12CC(CN[CH2:25]1)[CH2:21][N:20]([CH2:27][C@H:28]([OH:39])[CH2:29][O:30][C:31]1[CH:38]=[CH:37][C:34]([C:35]#[N:36])=[CH:33][CH:32]=1)[CH2:19]2.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl.C12CC(CNC1)CN(C(O)=O)C2.C([O-])([O-])=O.[K+].[K+]>C1COCC1>[CH:1]1([CH2:4][O:5][C:11]([N:13]2[CH2:14][CH:15]3[CH2:25][CH:18]([CH2:19][N:20]([CH2:27][C@H:28]([OH:39])[CH2:29][O:30][C:31]4[CH:38]=[CH:37][C:34]([C:35]#[N:36])=[CH:33][CH:32]=4)[CH2:21]3)[CH2:17]2)=[O:12])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 85 °C

Procedure

A cooled solution of cyclopropanemethanol (1.8 g; 25 mmol) in THF (7 mL) was added to a stirred 0C dispersion of CDI (4.05 g; 25 mmol) in THF (15 mL), and the reaction mixture was stirred for 30 minutes. A fraction of this solution (3.75 mL; 4.35 mmol) was added to a dispersion of 4-[3-(3,7-diazabicyclo[3.3.1]non-3-yl)-2(S)-hydroxypropoxy)benzonitrile (2.25 g; 6.0 mmol; dihydrochloride salt; prepared from 3,7-diazabicyclo[3.3.1]nonane-3-carboxylic acid and 7-[(2S)-3-(4-cyanophenoxy)-2-hydroxypropyl]-1,1-dimethylethyl ester, analogously to the method described in Example G above) and K2CO3 (2.0 g; 14.5 mmol) in THF (10 mL). The reaction mixture was heated (85° C.) in a sealed steel vessel for 24 hours, was then concentrated, and the residue partitioned between DCM and water. The organic layer was collected, dried, concentrated and subjected to column chromatography (DCM:MeOH; 95:5) to give the title compound in a 29% yield.

Workup

concentrationwas then concentrated
customthe residue partitioned between DCM and water
customThe organic layer was collected
customdried
concentrationconcentrated

Sources & evidence

ORD record: ord-a40108d2ec174c5f973227e457c9a15f
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06291475B1

Reaction notes

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