Hydrochloric Acid → HCID 178463673, compound

HRID 1911752Notes

Reaction equation

HRID 1911752 reaction equation
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[CH2:6][N:7]([C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=[C:12]([N:20]([CH2:23][CH:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:21][CH3:22])[CH:11]=1)[C:8]#[N:9].[N-:38]=[N+:39]=[N-:40].[Na+].O.Cl.[C:44](OCC)(=O)C>[Br-].[Zn+2].[Br-]>[F:35][C:32]([F:34])([F:33])[C:30]1[CH:29]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:37])[F:36])[CH:31]=1)[CH2:6][N:7]([CH2:10][C:11]1[C:12]([N:20]([CH2:23][CH:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:21][CH3:22])=[N:13][C:14]2[C:19]([CH:44]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]1[NH:9][N:40]=[N:39][N:38]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 57444441HCID 57444441, compound

Product 1

HCID 178463673HCID 178463673, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 10421208Zinc bromideCatalyst

Procedure

(3,5-Bis-trifluoromethyl-benzyl)-[2-(cyclopentylmethyl-ethyl-amino)-quinolin-4-yl]-cyanamide (0.368 g, 0.689 mmol), sodium azide (0.049 g, 0.758 mmol), and zinc bromide (0.155 g, 0.689 mmol) were added to a round bottom flask under a N2 atmosphere. To this reaction mixture, water (8 mL) was added, and the resulting mixture was refluxed for 24 h with vigorous stirring. Afterwards, the reaction mixture was cooled to RT and a mixture of HCl (3N, 0.92 mL) and ethyl acetate was added. The vigorous stirring was continued until no solid was separated out and the aqueous layer had reached a pH of 1. The organic layer was separated and concentrated under vacuum. A solution of sodium hydroxide (0.25N, 6.25 mL) was added to the residue and was stirred for 30 minutes until the residue was dissolved, and a suspension of zinc hydroxide was formed. The suspension was filtered and washed with NaOH (1N), and the filtrate was acidified with 3N HCl dropwise to afford (3-{[(3,5-bis-trifluoromethyl-benzyl)-(1H-tetrazol-5-yl)-amino]-methyl}-quinolin-2-yl)-cyclopentylmethyl-ethyl-amine as a yellow solid (0.140 g, yield: 35%).

Workup

  1. temperaturethe resulting mixture was refluxed for 24 h with vigorous stirring
  2. additionwas added
  3. customwas separated out
  4. customThe organic layer was separated
  5. concentrationconcentrated under vacuum
  6. additionA solution of sodium hydroxide (0.25N, 6.25 mL) was added to the residue
  7. stirringwas stirred for 30 minutes until the residue
  8. dissolutionwas dissolved
  9. additiona suspension of zinc hydroxide
  10. customwas formed
  11. filtrationThe suspension was filtered
  12. washwashed with NaOH (1N)

Sources & evidence

ORD record
ord-14bfe1048e194d468f282abd2fdf73a1
Source dataset
uspto-grants-2013_12
Patent number
US08604055B2

Reaction notes

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