Water → HCID 178491838, compound

HRID 1833131Notes

Reaction equation

HRID 1833131 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:3]=1[CH2:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:17][CH3:18])=[C:12]([O:15][CH3:16])[CH:13]=2)[C:8]([CH2:19][C:20]#[N:21])=[CH:7][N:6]=1.[N-:28]=[N+:29]=[N-:30].[Na+].Cl.C(N(CC)CC)C.[OH2:40]>C1(C)C=CC=CC=1.Cl>[CH3:18][O:17][C:11]1[CH:10]=[C:9]2[C:14](=[CH:13][C:12]=1[O:15][CH3:16])[C:5]([C:4]([C:3]1[CH:22]=[C:23]([O:26][CH3:27])[CH:24]=[CH:25][C:2]=1[F:1])=[O:40])=[N:6][CH:7]=[C:8]2[CH2:19][C:20]1[NH:30][N:29]=[N:28][N:21]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11130Triethylamine hydrochloride3×HCID 33557Sodium Azide3×HCID 22048314HCID 22048314, compound

Product 1

HCID 178491838HCID 178491838, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 1140TolueneSolvent2×

Procedure

183 mg (0.5 mmol) of [1-(2-Fluoro-5-methoxy-benzyl)-6,7-dimethoxy-isoquinolin-4-yl]-acetonitrile was dissolved in 15 mL toluene. The solution was warmed to 95 C. and 100 mg (1.53 mmol) of sodium azide and 210 mg (1.52 mmol) of triethyl amine hydrochloride was added and the mixture heated at 100 C for 60 minutes. Because ms and tlc suggest significant quantities of starting material is present an additional 100 mg of sodium azide and 210 mg of triethyl amine hydrochloride were added and heating at 100 C continued for 150 minutes at which time another 100 mg of sodium azide and 210 mg of triethyl amine hydrochloride and heating at 100 C continued for 120 minutes followed by room temperature stirring for 16 hours. The mixture was diluted with 15 mL of toluene and 20 mL of water. The stirring mixture was treated with 2 drops of conc. HCl in the fume hood and the resulting solid filtered giving ˜65 mg of the tetrazole as a white solid. The aqueous phase of the filtrate was separated and treated with stirring with another 2 drops of conc. HCl and solid filtered and washed with water to provide an additional 30 mg of the tetrazole. Thin layer chromatography show both crops to be homogeneous. Spectroscopy (nmr and ms) are compatible.

Workup

  1. temperatureThe solution was warmed to 95 C
  2. temperaturethe mixture heated at 100 C for 60 minutes
  3. additionwere added
  4. temperatureheating at 100 C
  5. waitcontinued for 120 minutes
  6. customfollowed by room temperature
  7. filtrationthe resulting solid filtered

Sources & evidence

ORD record
ord-75a939c6940541078d3b7ee663c5723e
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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