Ammonium Chloride → HCID 178461476, compound

HRID 536694Notes

Reaction equation

HRID 536694 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[NH4+].[Cl-].[N:7]1[C:11]2[CH:12]=[CH:13][C:14]([C:16]([N:18]3[CH2:25][CH2:24][C@:23]4([CH3:28])[C@H:26]([CH3:27])[C@H:19]3[CH2:20][C:21]3[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[CH:29][C:22]=34)=[O:17])=[CH:15][C:10]=2[NH:9][CH:8]=1>CN(C)C=O.O.CC#N>[N:7]1[C:11]2[CH:12]=[CH:13][C:14]([C:16]([N:18]3[CH2:25][CH2:24][C@:23]4([CH3:28])[C@H:26]([CH3:27])[C@H:19]3[CH2:20][C:21]3[CH:32]=[CH:31][C:30]([C:33]5[NH:34][N:3]=[N:2][N:1]=5)=[CH:29][C:22]=34)=[O:17])=[CH:15][C:10]=2[NH:9][CH:8]=1

Participants

7

Reactant 3

HCID 25517Ammonium Chloride2×HCID 33557Sodium Azide2×HCID 58375105HCID 58375105, compound

Product 1

HCID 178461476HCID 178461476, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of sodium azide (105 mg), NH4Cl (87 mg), and (2R,6R,11S)-3-(3H-benzoimidazole-5-carbonyl)-6,11-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocine-8-carbonitrile (0.30 g) in dimethylformamide (3 mL) is stirred at 100° C. overnight. Then, another portion of NaN3 (50 mg) and NH4Cl (40 mg) is added and the mixture is stirred at 110° C. for additional 14 h. After cooling to ambient temperature, the mixture is diluted with water and MeCN and purified by HPLC on reversed phase (MeCN/H2O/NH3).

Workup

  1. stirringthe mixture is stirred at 110° C. for additional 14 h
  2. temperatureAfter cooling to ambient temperature
  3. custompurified by HPLC on reversed phase (MeCN/H2O/NH3)

Sources & evidence

ORD record
ord-099e7818519841cda07e10ad2b47a052
Source dataset
uspto-grants-2014_10
Patent number
US08859580B2

Reaction notes

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