Ammonium Chloride → HCID 58795825, compound

HRID 1911756Notes

Reaction equation

HRID 1911756 reaction equation
[F:1][C:2]([F:39])([F:38])[C:3]1[CH:4]=[C:5]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1)[CH2:6][N:7]([CH2:10][C:11]1[C:12]([N:22]([CH2:27][CH:28]2[CH2:30][CH2:29]2)[CH2:23][CH:24]2[CH2:26][CH2:25]2)=[N:13][C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:21])[C:8]#[N:9].[N-:40]=[N+:41]=[N-:42].[Na+].[Cl-].[NH4+]>CN(C=O)C>[F:39][C:2]([F:38])([F:1])[C:3]1[CH:4]=[C:5]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1)[CH2:6][N:7]([CH2:10][C:11]1[C:12]([N:22]([CH2:23][CH:24]2[CH2:25][CH2:26]2)[CH2:27][CH:28]2[CH2:30][CH2:29]2)=[N:13][C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:21])[C:8]1[N:40]=[N:41][NH:42][N:9]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 86610066HCID 86610066, compound

Product 1

HCID 58795825HCID 58795825, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(3,5-Bis(trifluoromethyl)benzyl)-N-((2-(bis(cyclopropylmethyl)amino)-8-methylquinolin-3-yl)methyl)cyanamide (0.118 g, 0.216 mmol), sodium azide (0.70 g 1.08 mmol) and ammonium chloride (0.058 g, 1.08 mmol) were put in a RB flask under N2 atmosphere. To this reaction mixture, DMF (2 mL) was added and was refluxed for 1 h. The reaction mixture was cooled to RT and ice was added to this and extracted with ethylacetate (3×10 mL). The combined organic layer was washed with brine, dried over sodium sulphate and then concentrated under vacuum to afford of (3-{[(3,5-bistrifluoromethyl-benzyl)-(2H-tetrazol-5-yl)-amino]-methyl}-8-methyl-quinolin-2-yl)-bis-cyclopropylmethyl-amine as a yellow solid (0.125 g, 99%).

Workup

  1. temperaturewas refluxed for 1 h
  2. additionice was added to this and
  3. extractionextracted with ethylacetate (3×10 mL)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-78a9bdf0408e48ecb042f9ea72afcb20
Source dataset
uspto-grants-2013_12
Patent number
US08604055B2

Reaction notes

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