Potassium Carbonate → HCID 58116480, compound

HRID 661309Notes

Reaction equation

CO[CH2:3][CH2:4][O:5][C:6]1[N:10]=[C:9]([CH:11]2[CH2:16][CH:15]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[CH2:14][N:13]([C:28]([O:30]C3C=CC([N+]([O-])=O)=CC=3)=O)[CH2:12]2)[O:8][N:7]=1.Cl.[OH:41][CH:42]1[CH2:45][NH:44][CH2:43]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:4]([O:5][C:6]1[N:10]=[C:9]([CH:11]2[CH2:16][CH:15]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][C:24]([F:27])([F:25])[F:26])=[CH:19][CH:18]=3)[CH2:14][N:13]([C:28]([N:44]3[CH2:45][CH:42]([OH:41])[CH2:43]3)=[O:30])[CH2:12]2)[O:8][N:7]=1)[CH3:3]

Participants

Conditions

Temperature: 150 °C

Procedure

110 mg (0.211 mmol) of the compound from Example 67A, 69.3 mg (0.633 mmol) of 3-hydroxyazetidine hydrochloride and 72.9 mg (0.527 mmol) of potassium carbonate were added to 3.5 ml of DMF and heated in a single-mode microwave (Emrys Optimizer) at 150° C. for 20 min. For workup, the reaction solution was combined and filtered, and the residue was purified by means of preparative HPLC. Enantiomer separation of 47.7 mg of the racemate according to Method 8D gave 14.7 mg of the title compound from Example 96 (enantiomer 1) and 17.1 mg of the title compound from Example 97 (enantiomer 2).

Workup

filtrationfiltered
customthe residue was purified by means of preparative HPLC
customEnantiomer separation of 47.7 mg of the racemate

Sources & evidence

ORD record: ord-bb1e00f7c6584d40a262bf70b5dbb1ad
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084469B2

Reaction notes

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