Trisodium Phosphate → HCID 60098023, compound

HRID 2070345Notes

Reaction equation

HRID 2070345 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].Br[CH2:32][CH2:33][CH2:34][CH2:35][C:36](Cl)=[O:37].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][CH2:35][C:36]1=[O:37]

Participants

6

Reactant 4

HCID 24243Trisodium PhosphateHCID 5211735-Bromovaleryl chlorideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 131730049HCID 131730049, compound

Product 1

HCID 60098023HCID 60098023, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
100 °C

Procedure

To (4-{2-[(3-amino-4-chlorophenyl)amino]-1-methylbenzimidazol-5-yloxy}-(2-pyridyl))-N-methylcarboxamide in chloroform was added 5-bromopentanoylchloride (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 N-acylated product 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-oxopiperidin-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. concentrationThe mixture was concentrated
  5. custompartitioned between ethyl acetate and water
  6. customThe organic layer was dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f34c9f95d3dd4937bb801de68bd60b96
Source dataset
uspto-grants-2012_10
Patent number
US08299108B2

Reaction notes

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