Sodium Hydroxide → HCID 178428360, compound

HRID 248408Notes

Reaction equation

HRID 248408 reaction equation
C([C:5]1[N:14](CC2C=CC(N3C=C(Cl)C(Cl)=C3C#N)=CC=2)[C:8]2=[N:9][CH:10]=[CH:11][C:12]([CH3:13])=[C:7]2[N:6]=1)CCC.C[Sn](N=[N+]=[N-])(C)C.[OH-].[Na+]>C1(C)C(C)=CC=CC=1>[CH3:13][C:12]1[CH:11]=[CH:10][N:9]=[C:8]2[NH:14][CH:5]=[N:6][C:7]=12

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5104973Azido(trimethyl)stannaneHCID 19759303HCID 19759303, compound

Product 1

HCID 178428360HCID 178428360, compoundYield 346.7%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-butyl-3-[4-(3,4-dichloro-2-cyano-1-pyrrolyl)benzyl]-7-methyl-3H-imidazo[4,5-b]pyridine (490 mg) and trimethyltin azide (690 mg) in xylene (5 ml) was stirred at 120° C. for 22 hours. After cooled to ambient temperature, the mixture was treated with aqueous 1N sodium hydroxide (10 ml) for 4 hours. The suspension was filtered. The filtrate was washed with diisopropyl ether, adjusted to pH 4 with aqueous 1N-hydrochloric acid, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (elution by methanol/dichloromethane=1/8) to give 2-butyl-3-[4-[3,4-dichloro-2-(1H-tetrazol-5-yl)-1-pyrrolyl]benzyl]benzyl]-7-methyl-3H-imidazo[4,5-b]pyridine (516 mg) as an amorphous solid.

Workup

  1. temperatureAfter cooled to ambient temperature
  2. filtrationThe suspension was filtered
  3. washThe filtrate was washed with diisopropyl ether
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (elution by methanol/dichloromethane=1/8)

Sources & evidence

ORD record
ord-7709a99b21aa4b9f82284cc1f9f4c4ab
Source dataset
uspto-grants-1993_05
Patent number
US05210092

Reaction notes

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