Trifluoroacetic acid → 1-[4-{[(4-ethyl-2-pyridinyl)methyl]oxy}-3-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)phenyl]ethanone

HRID 63290Notes

Reaction equation

HRID 63290 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:28][CH2:29][C:30]2[CH:35]=[C:34]([CH2:36][CH3:37])[CH:33]=[CH:32][N:31]=2)=[C:8]([C:10]2[CH:27]=[CH:26][C:13]3[CH2:14][CH2:15][N:16](C(OC(C)(C)C)=O)[CH2:17][CH2:18][C:12]=3[CH:11]=2)[CH:9]=1)(=[O:3])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:36]([C:34]1[CH:33]=[CH:32][N:31]=[C:30]([CH2:29][O:28][C:7]2[CH:6]=[CH:5][C:4]([C:1](=[O:3])[CH3:2])=[CH:9][C:8]=2[C:10]2[CH:27]=[CH:26][C:13]3[CH2:14][CH2:15][NH:16][CH2:17][CH2:18][C:12]=3[CH:11]=2)[CH:35]=1)[CH3:37]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 706650431,1-dimethylethyl 7-(5-acetyl-2-{[(4-ethyl-2-pyridinyl)methyl]oxy}phenyl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

Product 1

HCID 706654121-[4-{[(4-ethyl-2-pyridinyl)methyl]oxy}-3-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)phenyl]ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl 7-(5-acetyl-2-{[(4-ethyl-2-pyridinyl)methyl]oxy}phenyl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate, (0.217 g) in DCM (3 ml) was added TFA (0.4 ml). This was stirred at room temperature. After completion of reaction by tlc, the reaction mixture was concentrated in vacuo and purified by preparative hplc. Product fractions were concentrated in vacuo and the product obtained was partitioned between DCM and aqueous sodium bicarbonate. The organics were dried over sodium sulphate and concentrated in vacuo to yield the title compound, 0.035 g

Workup

  1. customAfter completion of reaction by tlc
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. custompurified by preparative hplc
  4. concentrationProduct fractions were concentrated in vacuo
  5. customthe product obtained
  6. customwas partitioned between DCM and aqueous sodium bicarbonate
  7. dry with materialThe organics were dried over sodium sulphate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7311348bce3d43718f1bed12a30be8f0
Source dataset
uspto-grants-2016_09
Patent number
US09447074B2

Reaction notes

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