4-Methylmorpholine → HCID 178481039, compound

HRID 639385Notes

Reaction equation

HRID 639385 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]4[CH:28]=[CH:27][C:23]([C:24]([OH:26])=O)=[CH:22][CH:21]=4)[N:14]=3)=[CH:11][NH:10][N:9]=2)=[CH:4][CH:3]=1.CN1CCOCC1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[CH3:63][N:64]1[CH2:69][CH2:68][NH:67][CH2:66][CH2:65]1.C([O-])(O)=O.[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]4[CH:21]=[CH:22][C:23]([C:24]([N:67]5[CH2:68][CH2:69][N:64]([CH3:63])[CH2:65][CH2:66]5)=[O:26])=[CH:27][CH:28]=4)[N:14]=3)=[CH:11][NH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 531671-MethylpiperazineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 516892Sodium BicarbonateHCID 178524462HCID 178524462, compound

Product 1

HCID 178481039HCID 178481039, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the suspension of 600 mg (1.53 mMol; 1 Eq.) of 4-{4-[3-(4-chloro-phenyl)1H-pyrazol-4-yl]-pyrimidin-2-ylamino}-benzoic acid (Example 30) in 5 mL of DMF at rt is added 186 mg (202 μL; 1.83 mMol; 1.2 Eq.) of N-methylmorpholine ( Fluka 67869); 677 mg (1.53 mMol; 1 Eq.) of BOP (Fluka 12802) and 153 mg (170 μL; 1.53 mMol; I Eq.) of N-methylpiperazine (Fluka 68810). After 2 h at rt, the yellow solution is treated with 50 mL of NaHCO3 satd. solution and extracted with ethyl acetate. The combined organic layers are washed with water, dried (Na2SO4), filtered and concentrated under reduced pressure to approx. 10 mL. The precipitated crystals are collected, washed with a little ethyl acetate and dried at 60° C. under vacuum to obtain (4-{4-[3-(4-chloro-phenyl)-1H-pyrazol-4-yl]-pyrimidin-2-ylamino}-phenyl)-(4methyl-piperazin-1-yl)-methanone.

Workup

  1. extractionsolution and extracted with ethyl acetate
  2. washThe combined organic layers are washed with water
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure to approx. 10 mL
  6. customThe precipitated crystals are collected
  7. washwashed with a little ethyl acetate
  8. customdried at 60° C. under vacuum

Sources & evidence

ORD record
ord-e7949d105f0944e0989fff5bff92d942
Source dataset
uspto-grants-2010_04
Patent number
US07691855B2

Reaction notes

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