Trifluoroacetic acid → 7-(6-chloro-3-{[(4-methyl-2-pyridinyl)methyl]oxy}-2-pyridinyl)-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 63292Notes

Reaction equation

HRID 63292 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:25]=[CH:24][C:11]3[CH2:12][CH2:13][N:14](C(OC(C)(C)C)=O)[CH2:15][CH2:16][C:10]=3[CH:9]=2)[C:5]([O:26][CH2:27][C:28]2[CH:33]=[C:32]([CH3:34])[CH:31]=[CH:30][N:29]=2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:25]=[CH:24][C:11]3[CH2:12][CH2:13][NH:14][CH2:15][CH2:16][C:10]=3[CH:9]=2)[C:5]([O:26][CH2:27][C:28]2[CH:33]=[C:32]([CH3:34])[CH:31]=[CH:30][N:29]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 866705461,1-dimethylethyl 7-(6-chloro-3-{[(4-methyl-2-pyridinyl)methyl]oxy}-2-pyridinyl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

Product 1

HCID 866705457-(6-chloro-3-{[(4-methyl-2-pyridinyl)methyl]oxy}-2-pyridinyl)-2,3,4,5-tetrahydro-1H-3-benzazepine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cooled solution of 1,1-dimethylethyl 7-(6-chloro-3-{[(4-methyl-2-pyridinyl)methyl]oxy}-2-pyridinyl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate in DCM (1 ml) was added dropwise TFA (1 ml) and the reaction mixture stirred at room temperature until the starting material had been consumed. The reaction mixture was concentrated in vacuo, dissolved in water and backwashed with ethyl acetate. The aqueous layer was neutralised with aqueous sodium bicarbonate then extracted with ethyl acetate, dried over sodium sulphate and concentrated in vacuo to yield the title compound, 27 mg.

Workup

  1. customhad been consumed
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutiondissolved in water
  4. extractionthen extracted with ethyl acetate
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5363ba445693463dacc3b975f729e69d
Source dataset
uspto-grants-2016_09
Patent number
US09447074B2

Reaction notes

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