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Benzyl Bromide → Quinoline-6-carboxylic acid (2-benzyl-2H-tetrazol-5-ylmethyl)-amide

HRID 2080243
Notes
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Reaction equation

HRID 2080243 reaction equation
[N-]=[N+]=[N-].[Na+].[Cl-].[NH4+].C(CNC(C1C=C2C(=CC=1)N=CC=C2)=O)#N.[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].[N:37]1[NH:38][N:39]=[N:40][C:41]=1[CH2:42][NH:43][C:44]([C:46]1[CH:47]=[C:48]2[C:53](=[CH:54][CH:55]=1)[N:52]=[CH:51][CH:50]=[CH:49]2)=[O:45]>CN(C)C=O.C(OCC)(=O)C.O>[CH2:23]([N:38]1[N:39]=[N:40][C:41]([CH2:42][NH:43][C:44]([C:46]2[CH:47]=[C:48]3[C:53](=[CH:54][CH:55]=2)[N:52]=[CH:51][CH:50]=[CH:49]3)=[O:45])=[N:37]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 6

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 55126745quinoline-6-carboxylic acid (2H-tetrazol-5-ylmethyl)amideHCID 58388078Quinoline-6-carboxylic acid cyanomethyl-amide

Product 1

HCID 58875321
Quinoline-6-carboxylic acid (2-benzyl-2H-tetrazol-5-ylmethyl)-amide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Sodium azide (260 mg, 4.0 mmol) and ammonium chloride (210 mg, 4.0 mmol) were suspended in a solution of quinoline-6-carboxylic acid cyanomethyl-amide described in Preparation Example E-1 (420 mg, 2.0 mmol) in N,N-dimethylformamide (15 mL), and the solution was stirred at 100° C. for 12 hours. Benzyl bromide (0.12 mL, 1.0 mmol) and potassium carbonate (400 mg, 3.0 mmol) were added to a solution having half the amount of the solution containing quinoline-6-carboxylic acid (2H-tetrazol-5-ylmethyl)amide obtained, which was then stirred for 20 minutes at 50° C. Water and ethyl acetate were added to the reaction solution, which was then partitioned, NH silica gel was added to the organic layer, and the solvent was evaporated in vacuo for adsorption, purification was carried out by NH silica gel column chromatography, and the title compound (20 mg, 0.058 mmol) was obtained as a white solid.

Workup

  1. customobtained
  2. stirringwhich was then stirred for 20 minutes at 50° C
  3. customwas then partitioned
  4. additionNH silica gel was added to the organic layer
  5. customthe solvent was evaporated in vacuo for adsorption, purification

Sources & evidence

ORD record
ord-1408cdae9fdb44e2905ac3ed7aff3acb
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07932272B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes