Dichloromethane → HCID 68540110, compound

HRID 1993704Notes

Reaction equation

HRID 1993704 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:17][C:18]([NH:20][C:21]2[CH:22]=[N:23][C:24]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[C:25]([CH3:27])[CH:26]=2)=[O:19])[N:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].Cl.CN(C)CCCN=C=NCC.[F:46][C:47]1[CH:55]=[CH:54][CH:53]=[C:52]([F:56])[C:48]=1[C:49](O)=[O:50].C(Cl)Cl>C(#N)C.O>[C:1]([C:5]1[CH:6]=[C:7]([NH:17][C:18]([NH:20][C:21]2[CH:22]=[N:23][C:24]([N:28]3[CH2:29][CH2:30][N:31]([C:49](=[O:50])[C:48]4[C:47]([F:46])=[CH:55][CH:54]=[CH:53][C:52]=4[F:56])[CH2:32][CH2:33]3)=[C:25]([CH3:27])[CH:26]=2)=[O:19])[N:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 97962,6-Difluorobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68538027HCID 68538027, compound

Product 1

HCID 68540110HCID 68540110, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Place 1-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-(5-methyl-6-piperazin-1-yl-pyridin-3-yl)-urea (300 mg, 0.670 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (154 mg, 0.804 mmol), 2,6-difluorobenzoic acid (127 mg, 0.804 mmol), and 4-N,N-dimethylaminopyridine (15 mg, 0.134 mmol) in acetonitrile (10 mL). Heat the reaction to 60° C. for 18 hours. Cool reaction to room temperature and add CH2Cl2 and water. Separate organic layer and extract aqueous layer with CH2Cl2 (2×20 mL). Combine organic layers, dry over Mg2SO4, filter, and concentrate under reduced pressure. Subject residue to silica gel chromatography eluting with 10-70% EtOAc:hexane to yield the title compound. MS(ES+): m/z=588.3 [M+H].

Workup

  1. temperatureHeat
  2. customthe reaction to 60° C. for 18 hours
  3. temperatureCool
  4. customreaction to room temperature
  5. extractionSeparate organic layer and extract aqueous layer with CH2Cl2 (2×20 mL)
  6. dry with materialCombine organic layers, dry over Mg2SO4
  7. filtrationfilter
  8. concentrationconcentrate under reduced pressure
  9. washSubject residue to silica gel chromatography eluting with 10-70% EtOAc

Sources & evidence

ORD record
ord-d8a647e1affc4949a67e899983bba695
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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