Cesium carbonate → HCID 58335522, compound

HRID 1890685Notes

Reaction equation

HRID 1890685 reaction equation
Cl.Cl[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.[F:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[CH:19]1[CH2:23][CH2:22][CH2:21][N:20]1[C:24]1[CH:25]=[CH:26][C:27]2[N:28]([C:30]([C:33]3[CH:34]=[N:35][NH:36][CH:37]=3)=[CH:31][N:32]=2)[N:29]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[F:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[CH:19]1[CH2:23][CH2:22][CH2:21][N:20]1[C:24]1[CH:25]=[CH:26][C:27]2[N:28]([C:30]([C:33]3[CH:37]=[N:36][N:35]([CH2:3][CH2:4][N:5]4[CH2:10][CH2:9][O:8][CH2:7][CH2:6]4)[CH:34]=3)=[CH:31][N:32]=2)[N:29]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 135998176HCID 135998176, compound

Product 1

HCID 58335522HCID 58335522, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In step 7-2, 4-(2-chloroethyl)morpholine hydrochloride (40 mg, 0.2 mmol) was added to a solution of 6-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)-3-(1H-pyrazol-4-yl)imidazo[1,2-b]pyridazine (7-1) (35 mg, 0.1 mmol) and cesium carbonate (100 mg, 0.35 mmol) in DMF (5 mL). The reaction mixture was stirred at room temperature over-night and the DMF was then removed using a rotary evaporator. The resulting residue was reconstituted in ethyl acetate (30 mL) and the organic layer extracted with brine and then dried using sodium sulfate. The ethyl acetate was removed and the product was further purify by preparative LC/MS to yield 4-(2-(4-(6-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)imidazo[1,2-b]pyridazin-3-yl)-1H-pyrazol-1-yl)ethyl)morpholine (7-2) as a white solid. m/z=480.2 [M+1].

Workup

  1. customthe DMF was then removed
  2. customa rotary evaporator
  3. extractionthe organic layer extracted with brine
  4. customdried
  5. customThe ethyl acetate was removed
  6. customthe product was further purify by preparative LC/MS

Sources & evidence

ORD record
ord-8c97fa08d2524ddd9c2f1f8346d789f8
Source dataset
uspto-grants-2013_08
Patent number
US08507488B2

Reaction notes

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