Trisodium Phosphate → HCID 60098079, compound

HRID 2070344Notes

Reaction equation

HRID 2070344 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:14]([CH3:15])[C:13]3[CH:16]=[CH:17][C:18]([O:20][C:21]4[CH:26]=[CH:25][N:24]=[C:23]([C:27]([NH:29][CH3:30])=[O:28])[CH:22]=4)=[CH:19][C:12]=3[N:11]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl[CH2:32][CH2:33][CH2:34][C:35](Cl)=[O:36].P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+].C[Si]([N-][Si](C)(C)C)(C)C.[K+]>C(Cl)(Cl)Cl>[Cl:8][C:7]1[CH:6]=[CH:5][C:4]([NH:9][C:10]2[N:14]([CH3:15])[C:13]3[CH:16]=[CH:17][C:18]([O:20][C:21]4[CH:26]=[CH:25][N:24]=[C:23]([C:27]([NH:29][CH3:30])=[O:28])[CH:22]=4)=[CH:19][C:12]=3[N:11]=2)=[CH:3][C:2]=1[N:1]1[CH2:32][CH2:33][CH2:34][C:35]1=[O:36]

Participants

6

Reactant 4

HCID 24243Trisodium PhosphateHCID 783704-Chlorobutyryl chlorideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 131730049HCID 131730049, compound

Product 1

HCID 60098079HCID 60098079, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To (4-{2-[(3-amino-4-chlorophenyl)amino]-1-methylbenzimidazol-5-yloxy}-(2-pyridyl))-N-methylcarboxamide in chloroform was added 4-chlorobutanoylchloride (1.5 eq) and sodium phosphate (3 eq) and stir for 2 hours. Acylation was checked by HPLC/MS. The mixture was partitioned between methylene chloride and water. The organic layer was dried with sodium sulfate and concentrated. The crude was taken in tetrahydrofuran and Potassiumbis(trimethylsilyl)amide (2 eq) was added to it and the mixture was heated at 100 C for 16 h. The mixture was concentrated and partitioned between ethyl acetate and water. The organic layer was dried and concentrated to give 4-[(2-{[4-chloro-3-(2-oxopyrrolidin-1-yl)phenyl]amino}-1-methyl-1H-benzimidazol-5-yl)oxy]-N-methylpyridine-2-carboxamide.

Workup

  1. customThe mixture was partitioned between methylene chloride and water
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. concentrationconcentrated
  4. temperaturethe mixture was heated at 100 C for 16 h
  5. concentrationThe mixture was concentrated
  6. custompartitioned between ethyl acetate and water
  7. customThe organic layer was dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-8e66cfb8c9d743c3b71360f39d070d2e
Source dataset
uspto-grants-2012_10
Patent number
US08299108B2

Reaction notes

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