Cesium carbonate → HCID 71473972, compound

HRID 1468860Notes

Reaction equation

HRID 1468860 reaction equation
Cl.[F:2][C:3]1[CH:20]=[C:19]([S:21]([CH3:24])(=[O:23])=[O:22])[CH:18]=[CH:17][C:4]=1[CH2:5][O:6][CH2:7][C@@H:8]1[CH2:10][C@@H:9]1[CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.[C:25]([O-:28])([O-])=O.[Cs+].[Cs+].Cl[C:32]1[CH:37]=[CH:36][N:35]=[C:34](C=O)[N:33]=1>CS(C)=O.CCOC(C)=O>[F:2][C:3]1[CH:20]=[C:19]([S:21]([CH3:24])(=[O:23])=[O:22])[CH:18]=[CH:17][C:4]=1[CH2:5][O:6][CH2:7][C@@H:8]1[CH2:10][C@@H:9]1[CH:11]1[CH2:12][CH2:13][N:14]([C:34]2[N:35]=[CH:36][C:37]([CH:25]=[O:28])=[CH:32][N:33]=2)[CH2:15][CH2:16]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 513419564-Chloropyrimidine-2-carbaldehydeHCID 86717796HCID 86717796, compound

Product 1

HCID 71473972HCID 71473972, compoundYield 67.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

4-((1R,2R)-2-(((2-fluoro-4-(methylsulfonyl)benzyl)oxy)methyl)cyclopropyl)piperidine hydrochloride (Step D product) was dissolved in DMSO (7 ml) at RT under N2 and Cs2CO3 (539 mg, 1.654 mmol) was added. The mixture was stirred at RT for 5 min and chloropyrimidine aldehyde (113 mg, 0.794 mmol) in DMSO (1 mL) was added. The mixture was stirred at RT overnight. The mixture was diluted with EtOAc, washed with sat. NH4Cl, dried over MgSO4, evaporated to dryness. The crude material was purified by flash column (25 g SNAP, 25˜60% EtOAc in hexane) to afford 200 mg of the desired product (67.6%) as a white solid. LC/MS (m/z): 448 (M+H)+.

Workup

  1. stirringThe mixture was stirred at RT overnight
  2. washwashed with sat. NH4Cl
  3. dry with materialdried over MgSO4
  4. customevaporated to dryness
  5. customThe crude material was purified by flash column (25 g SNAP, 25˜60% EtOAc in hexane)

Sources & evidence

ORD record
ord-b450dba99b7649248859593ce75002a1
Source dataset
uspto-grants-2015_04
Patent number
US09006228B2

Reaction notes

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