Potassium Carbonate → HCID 58116483, compound

HRID 661310Notes

Reaction equation

HRID 661310 reaction equation
[CH3:1][O:2][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](OC3C=CC([N+]([O-])=O)=CC=3)=[O:29])[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>[OH:41][CH:42]1[CH2:45][N:44]([C:28]([N:13]2[CH2:14][CH:15]([C:17]3[CH:18]=[CH:19][C:20]([CH2:23][C:24]([F:26])([F:25])[F:27])=[CH:21][CH:22]=3)[CH2:16][CH:11]([C:9]3[O:8][N:7]=[C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[N:10]=3)[CH2:12]2)=[O:29])[CH2:43]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27592903-Hydroxyazetidine hydrochlorideHCID 58116569HCID 58116569, compound

Product 1

HCID 58116483HCID 58116483, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

50.5 mg (0.064 mmol, purity 70%) of the compound from Example 67A, 30.2 mg (0.275 mmol) of 3-hydroxyazetidine hydrochloride and 31.7 mg (0.229 mmol) of potassium carbonate were added to 2.1 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 100 mg of the racemic crude product according to Method 8D gave 7.8 mg of the title compound from Example 98 (enantiomer 1) and 8.0 mg of the title compound from Example 99 (enantiomer 2).

Workup

  1. filtrationfiltered
  2. customthe residue was purified by means of preparative HPLC
  3. customEnantiomer separation of 100 mg of the racemic crude product

Sources & evidence

ORD record
ord-85ebb5418d0d4f538bfe8a9fa10daf82
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

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