Water → HCID 58588084, compound

HRID 1361662Notes

Reaction equation

HRID 1361662 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([NH:15][C:16](=[O:37])[C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([NH:24][C:25]3[C:30]([C:31]4[CH:36]=[CH:35][N:34]=[CH:33][N:32]=4)=[CH:29][CH:28]=[CH:27][N:26]=3)[CH:18]=2)[CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1.[CH3:38][N:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1.[I-].[Na+].O>CN(C=O)C>[CH3:23][C:20]1[CH:21]=[CH:22][C:17]([C:16]([NH:15][C:7]2[CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=[C:5]([O:4][CH2:3][CH2:2][N:42]3[CH2:43][CH2:44][N:39]([CH3:38])[CH2:40][CH2:41]3)[CH:6]=2)=[O:37])=[CH:18][C:19]=1[NH:24][C:25]1[C:30]([C:31]2[CH:36]=[CH:35][N:34]=[CH:33][N:32]=2)=[CH:29][CH:28]=[CH:27][N:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 531671-MethylpiperazineHCID 58588549HCID 58588549, compound

Product 1

HCID 58588084HCID 58588084, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of N-(3-(2-chloroethoxy)-5-(trifluoromethyl)phenyl)-4-methyl-3-(3-(pyrimidin-4-yl)pyridin-2-ylamino)benzamide (200 mg, 0.38 mmol), 1-methylpiperazine (76 mg, 0.76 mmol) and sodium iodide (catalytic amount) in DMF (5 ml) was heated at 100° C. for 20 hr. After cooling to RT, water (50 ml) was added and the mixture was extracted with EtOAc (3×50 ml). The combined organic layer was washed with brine (3×50 ml) and dried over Na2SO4. The solvent was removed in vacuo and the product was purified by flash column chromatography eluting with MeOH(NH3)/DCM (1 to 5%) to afford the title compound as a light yellow solid. MS m/z=592 [M+1]+. Calc'd for C31H32F3N7O2: 591.6.

Workup

  1. temperatureAfter cooling to RT
  2. extractionthe mixture was extracted with EtOAc (3×50 ml)
  3. washThe combined organic layer was washed with brine (3×50 ml)
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed in vacuo
  6. customthe product was purified by flash column chromatography
  7. washeluting with MeOH(NH3)/DCM (1 to 5%)

Sources & evidence

ORD record
ord-a098ec43ef634ef3bd9011bbaeaefb18
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

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