Cesium carbonate → HCID 66669839, compound

HRID 1517904Notes

Reaction equation

HRID 1517904 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:20]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[C:21]([C:23]2([C:26]([NH2:28])=[O:27])[CH2:25][CH2:24]2)=[O:22])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([OH:19])=[CH:16][CH:17]=2)[N:12]=[CH:11][CH:10]=1.[OH:36][CH:37]1[C:41]2([CH2:43][CH2:42]2)[CH2:40][N:39]([CH2:44][CH2:45][CH2:46]CS([O-])(=O)=O)[CH2:38]1.C([O-])([O-])=O.[Cs+].[Cs+]>CC(N(C)C)=O>[OH:36][CH:37]1[C:41]2([CH2:43][CH2:42]2)[CH2:40][N:39]([CH2:44][CH2:45][CH2:46][O:19][C:15]2[CH:14]=[C:13]3[C:18]([C:9]([O:8][C:7]4[CH:6]=[CH:5][C:4]([N:20]([C:29]5[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=5)[C:21]([C:23]5([C:26]([NH2:28])=[O:27])[CH2:25][CH2:24]5)=[O:22])=[CH:3][C:2]=4[F:1])=[CH:10][CH:11]=[N:12]3)=[CH:17][CH:16]=2)[CH2:38]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 86645607HCID 86645607, compoundHCID 136346387HCID 136346387, compound

Product 1

HCID 66669839HCID 66669839, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of N-(3-fluoro-4-(7-hydroxy-quinolin-4-yloxy)phenyl)-N-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide (266 mg, 0.56 mmol) in DMA (3 mL) was added 3-(7-hydroxy-5-azaspiro[2.4]heptane-5-yl)propylmethanesulfonate (283 mg, 1.14 mmol) and Cs2CO3 (556 mg, 1.71 mmol). The reaction was then stirred at rt for 2 days. The solvent was then removed and the residue was partioned between saturated NaHCO3 aqueous solution (15 mL) and CHCl3 (30 mL). The organic layer was separated, dried over anhydrous Na2SO4, filtered. The filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (100:15:1(v/v/v) EtOAc/CH3OH/Et3N) to afford the title compound as a white solid (290 mg, 82%).

Workup

  1. customThe solvent was then removed
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customThe residue was purified by a silica gel column chromatography (100:15:1(v/v/v) EtOAc/CH3OH/Et3N)

Sources & evidence

ORD record
ord-ccac09a60b7c4958896a4b858321c2db
Source dataset
uspto-grants-2012_07
Patent number
US08232294B2

Reaction notes

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