Hydrochloric Acid → HCID 178501566, compound

HRID 2254124Notes

Reaction equation

HRID 2254124 reaction equation
[NH:1]1[C:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[C:12]2[CH:17]=[CH:16][C:15]([CH2:18][NH:19][C:20]3[C:29]4[CH2:28][CH2:27][CH2:26][CH2:25][C:24]=4[N:23]=[C:22]([C:30]([F:33])([F:32])[F:31])[N:21]=3)=[CH:14][CH:13]=2)=[N:4][N:3]=[N:2]1.[H-].[Na+].C1(C(Cl)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[CH2:57][C:58]([O:60][CH3:61])=[O:59].Cl>CN(C=O)C.O.O1CCOCC1>[CH3:61][O:60][C:58](=[O:59])[CH2:57][N:19]([CH2:18][C:15]1[CH:16]=[CH:17][C:12]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:5]2[NH:1][N:2]=[N:3][N:4]=2)=[CH:13][CH:14]=1)[C:20]1[C:29]2[CH2:28][CH2:27][CH2:26][CH2:25][C:24]=2[N:23]=[C:22]([C:30]([F:32])([F:33])[F:31])[N:21]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6456Trityl chlorideHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 1785062715,6,7,8-tetrahydro-N-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-2-(trifluoromethyl)-4-quinazolinamine

Product 1

HCID 178501566HCID 178501566, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

To a 0° C. solution of 0.01 mmol of 5,6,7,8-tetrahydro-N-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-2-(trifluoromethyl)-4-quinazolinamine in 10 mL of anhydrous DMF was added 0.01 mmol of NaH. The resulting solution was stirred at 0° C. for 30 minutes at which time 0.01 mmol of triphenylmethylchloride was added. The reaction mixture was stirred at room temperature for 18 hours and 0.01 mmol of methyl bromoacetate was added. After 24 hours the reaction mixture was diluted with water and extracted with ethyl acetate (3×10 mL). The organic phase was extracted with brine, dried over anhydrous magnesium sulfate, filtered and evaporated to yield a residue which was treated with 2N HCl in dioxane. The solvents were evaporated and the resulting residue was purified on silica to yield the title compound.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate (3×10 mL)
  3. extractionThe organic phase was extracted with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto yield a residue which
  8. customThe solvents were evaporated
  9. customthe resulting residue was purified on silica

Sources & evidence

ORD record
ord-0633c60b0e794137bb6099873d296fda
Source dataset
uspto-grants-1993_08
Patent number
US05234936

Reaction notes

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