Sodium Chloride → HCID 21949172, compound

HRID 2376883Notes

Reaction equation

HRID 2376883 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C:12]3[CH:17]=[CH:16][N:15]=[C:14]([NH2:18])[CH:13]=3)=[CH:8][CH:9]=2)[C:4]([Cl:19])=[C:3]1C(N)=O.[Cl-].[Na+].Cl[C:26]([O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:27].C(=O)([O-])[OH:36].[Na+].[CH3:40][N:41](C)C=O>N1C=CC=CC=1.C(N(CC)CC)C>[Cl:19][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([O:11][C:12]3[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C:26](=[O:27])[O:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH:13]=3)[CH:6]=2)[N:2]([C:1]([NH:41][CH3:40])=[O:36])[CH:3]=1

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 6228DimethylformamideHCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 69312861HCID 69312861, compound

Product 1

HCID 21949172HCID 21949172, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8471TriethylamineSolvent

Procedure

While a mixture of N1-methyl-5-(2-amino-4-pyridyl)oxy-3-chloro-1H-1-indolecarboxamide (850 mg, Production example 102-1), triethylamine (0.37 ml), pyridine (320 mg) and N,N-dimethylformamide (10 ml) was cooled with ice and sodium chloride, phenyl chloroformate (630 mg) was added dropwise to the mixture. Aqueous solution of sodium hydrogencarbonate was added thereto after stirring for 20 minutes; extraction was performed with ethyl acetate; and purification was performed by silica gel column chromatography (ethyl acetate). The crystals precipitated by adding ethyl acetate to the residue were filtered off to yield the title compound as white crystals (160 mg).

Workup

  1. additionwas added dropwise to the mixture
  2. extractionextraction
  3. customand purification
  4. customThe crystals precipitated
  5. additionby adding ethyl acetate to the residue
  6. filtrationwere filtered off

Sources & evidence

ORD record
ord-0266ec46f8374e7f9e9d323480ae01e9
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

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