Hydrochloric Acid → HCID 178429020, compound

HRID 2363211Notes

Reaction equation

HRID 2363211 reaction equation
[C:1]([CH2:3][NH:4][C:5](=[O:37])[C:6]1[CH:11]=[CH:10][C:9]([CH:12]([O:18][C:19]2[CH:24]=[C:23]([CH3:25])[C:22]([C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=3)=[C:21]([CH3:36])[CH:20]=2)[CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:8][CH:7]=1)#[N:2].Cl.C(N(CC)CC)C.[N-:46]=[N+:47]=[N-:48].[Na+].Cl>C1(C)C=CC=CC=1.O>[CH3:36][C:21]1[CH:20]=[C:19]([O:18][CH:12]([C:9]2[CH:8]=[CH:7][C:6]([C:5]([NH:4][CH2:3][C:1]3[NH:48][N:47]=[N:46][N:2]=3)=[O:37])=[CH:11][CH:10]=2)[CH2:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH:24]=[C:23]([CH3:25])[C:22]=1[C:26]1[CH:27]=[CH:28][C:29]([C:32]([F:35])([F:33])[F:34])=[CH:30][CH:31]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 86631571HCID 86631571, compound

Product 1

HCID 178429020HCID 178429020, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

N-Cyanomethyl-4-[1-(2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-yloxy)-3,3-dimethyl-butyl]-benzamide (160 mg, 0.32 mmol) is dissolved in toluene (20 mL). Triethylamine hydrochloride (132 mg, 0.96 mmol) is added followed by sodium azide (62 mg, 0.96 mmol) and then the reaction is refluxed for 24 h. The mixture is allowed to cool to room temperature, poured into water and adjusted to pH=3 with aqueous HCl. The product is extracted into ethyl acetate, dried, and concentrated to give 145 mg (82%) of the titled compound. MS (ES): 552.2 [M+1]+, 550.2 [M−1]−.

Workup

  1. temperaturethe reaction is refluxed for 24 h
  2. extractionThe product is extracted into ethyl acetate
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-91e5049e9f2d4c219bb34bbc92132756
Source dataset
uspto-grants-2014_04
Patent number
US08691856B2

Reaction notes

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