Triethylamine → HCID 42603195, compound

HRID 659041Notes

Reaction equation

HRID 659041 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[C:15]1[NH:19][N:18]=[N:17][N:16]=1.C(N(CC)CC)C.Cl.Cl[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=1>CN(C)C(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[C:15]1[N:19]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)[N:18]=[N:17][N:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 23392Picolyl chloride hydrochloride2×HCID 178486844HCID 178486844, compound

Product 1

HCID 42603195HCID 42603195, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
27.5 °C

Procedure

Experimental Procedure: 50.0 ml of N,N-dimethyl acetamide and 5.0 g (0.019 mol) of 6,7-dimethoxy-4-(1H-tetrazol-5-yl)quinazoline were charged into a 250 ml of 4 necked round bottom flask, connected to a mechanical stirrer, thermometer socket, condenser and addition flask under mild nitrogen atmosphere. 3.80 g (0.038 mol) of triethyl amine was added at 25-30° C. Stirred the mass for 15-20 min at 25-30° C. Reaction mass temperature was raised to 50-55° C. Maintained the mass temperature at 50-55° C. for 15-20 min. 2-chloro methylpyridine hydrochloride solution [3.20 g (0.019 mol) 2-chloro methylpyridine hydrochloride was dissolved in 25.0 ml of N,N-dimethyl acetamide] was added slowly at 50-55° C. for 30-45 min. Maintained the mass temperature at 50-55° C. for 15-20 min. Raised the mass temperature to 80-85° C. Maintained the mass temperature at 80-85° C. for 7-8 hours. N,N-dimethyl acetamide was completely distilled off under vacuum. Crude compound was purified by the column chromatography by using hexane and ethyl acetate. Obtained 1.90 g (yield 28.0% by theory) of pure compound weight.

Workup

  1. customconnected to a mechanical stirrer
  2. additionthermometer socket, condenser and addition flask under mild nitrogen atmosphere
  3. customReaction mass temperature
  4. temperaturewas raised to 50-55° C
  5. temperatureMaintained the mass temperature at 50-55° C. for 15-20 min
  6. temperatureMaintained the mass temperature at 50-55° C. for 15-20 min
  7. temperatureRaised the mass temperature to 80-85° C
  8. temperatureMaintained the mass temperature at 80-85° C. for 7-8 hours
  9. distillationN,N-dimethyl acetamide was completely distilled off under vacuum
  10. customCrude compound was purified by the column chromatography
  11. customObtained 1.90 g (yield 28.0% by theory) of pure compound weight

Sources & evidence

ORD record
ord-e8946e8b668d4a569a4b8b4c48f38a79
Source dataset
uspto-grants-2011_12
Patent number
US08080558B2

Reaction notes

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