2-Chloro-N,N-dimethylethylamine → 5-[2-(dimethylamino)ethoxy]-2-[1-[(4-ethoxy-2,6-difluorophenyl)methyl]-5,6-dihydro-4H-cyclopenta[c]pyrazol-3-yl]-N-pyridin-4-ylpyrimidin-4-amine

HRID 1482933Notes

Reaction equation

HRID 1482933 reaction equation
[CH2:1]([O:3][C:4]1[CH:32]=[C:31]([F:33])[C:7]([CH2:8][N:9]2[C:13]3[CH2:14][CH2:15][CH2:16][C:12]=3[C:11]([C:17]3[N:22]=[C:21]([NH:23][C:24]4[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=4)[C:20]([OH:30])=[CH:19][N:18]=3)=[N:10]2)=[C:6]([F:34])[CH:5]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:42][CH2:43][N:44]([CH3:46])[CH3:45]>CN(C=O)C>[CH3:45][N:44]([CH3:46])[CH2:43][CH2:42][O:30][C:20]1[C:21]([NH:23][C:24]2[CH:25]=[CH:26][N:27]=[CH:28][CH:29]=2)=[N:22][C:17]([C:11]2[C:12]3[CH2:16][CH2:15][CH2:14][C:13]=3[N:9]([CH2:8][C:7]3[C:6]([F:34])=[CH:5][C:4]([O:3][CH2:1][CH3:2])=[CH:32][C:31]=3[F:33])[N:10]=2)=[N:18][CH:19]=1

Participants

5

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 11430Potassium CarbonateHCID 1362464902-[1-(4-Ethoxy-2,6-difluorobenzyl)-1,4,5,6-tetrahydrocyclopenta-[c]pyrazol-3-yl]-4-(pyridin-4-ylamino)pyrimidin-5-ol

Product 1

HCID 722026965-[2-(dimethylamino)ethoxy]-2-[1-[(4-ethoxy-2,6-difluorophenyl)methyl]-5,6-dihydro-4H-cyclopenta[c]pyrazol-3-yl]-N-pyridin-4-ylpyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

100 mg of 2-[1-(4-ethoxy-2,6-difluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[c]-pyrazol-3-yl]-4-(pyridin-4-ylamino)pyrimidin-5-ol 2-2-1 (0.215 mmol, 1.00 eq.) were dissolved in 8 mL of dry DMF and 149 mg potassium carbonate (1.08 mmol, 5.00 eq.) and 47 mg 2-chloro-N,N-dimethylethanamine (0.323 mmol, 1.50 eq.) were added. The reaction mixture was stirred over night at 50° C. The reaction mixture was partitioned between aqueous half saturated sodium chloride solution and DCM/isopropanol (4:1). The separated aqueous layer was extracted with DCM/isopropanol (4:1). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The purification of the residue by flash chromatography provided 51 mg (0.09 mmol, 42%) of analytically pure target compound.

Workup

  1. customThe reaction mixture was partitioned between aqueous half saturated sodium chloride solution and DCM/isopropanol (4:1)
  2. extractionThe separated aqueous layer was extracted with DCM/isopropanol (4:1)
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe purification of the residue by flash chromatography
  6. customprovided 51 mg (0.09 mmol, 42%) of analytically pure target compound

Sources & evidence

ORD record
ord-4719120e5b4944e1a1d92b1bff29b8ea
Source dataset
uspto-grants-2016_08
Patent number
US09416125B2

Reaction notes

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