Sodium Azide → HCID 86691444, compound

HRID 540330Notes

Reaction equation

HRID 540330 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([N:16]2[CH2:22][CH2:21][CH2:20][C:19]3[CH:23]=[CH:24][CH:25]=[CH:26][C:18]=3[CH2:17]2)[CH:7]=1)=[O:4].[N-:27]=[N+:28]=[N-:29].[Na+]>C(#N)C.C(OCC)(=O)C>[N:27]([CH2:2][C:3]([NH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([N:16]2[CH2:22][CH2:21][CH2:20][C:19]3[CH:23]=[CH:24][CH:25]=[CH:26][C:18]=3[CH2:17]2)[CH:7]=1)=[O:4])=[N+:28]=[N-:29]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86691443HCID 86691443, compound

Product 1

HCID 86691444HCID 86691444, compoundYield 91.9%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-chloro-N-[2-(1,3,4,5-tetrahydro-2H-2-benzazepin-2-yl)quinolin-4-yl]acetamide (70 mg, 0.19 mmol) in acetonitrile (2 mL) was added sodium azide (62 mg, 0.95 mmol). The resulting mixture was stirred at room temperature for 6 hours. The reaction was diluted with ethyl acetate (20 mL), and then washed with water (10 mL). The ethyl acetate fraction was dried over sodium sulfate, and then concentrated under reduced pressure to give a residue which was purified by column chromatography on silica gel (ethyl acetate/petroleum ether, 1:4) to give 65 mg of product as a white powder (yield was 91.8%). MS obsd. (ESI+) [(M+H)+] 373.

Workup

  1. washwashed with water (10 mL)
  2. dry with materialThe ethyl acetate fraction was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto give a residue which
  5. customwas purified by column chromatography on silica gel (ethyl acetate/petroleum ether, 1:4)

Sources & evidence

ORD record
ord-6d6a0b7bd31048549f28ec91729aa007
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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