Trifluoroacetic acid → 7-(1,3-Dimethyl-1H-pyrazol-5-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 1674491Notes

Reaction equation

HRID 1674491 reaction equation
CC([CH:5]1[C:11]2[CH:12]=[CH:13][C:14]([C:16](=O)[CH2:17]/[C:18](=[N:20]/[N:21]([C:23](OC(C)(C)C)=O)C)/[CH3:19])=[CH:15][C:10]=2[CH2:9][CH2:8][N:7](C([O-])=O)[CH2:6]1)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:23][N:21]1[C:16]([C:14]2[CH:13]=[CH:12][C:11]3[CH2:5][CH2:6][NH:7][CH2:8][CH2:9][C:10]=3[CH:15]=2)=[CH:17][C:18]([CH3:19])=[N:20]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178450040HCID 178450040, compound2×

Product 1

HCID 251050497-(1,3-Dimethyl-1H-pyrazol-5-yl)-2,3,4,5-tetrahydro-1H-3-benzazepineYield 98.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1,1-dimethylethyl-7-{(3E)-3-[{[(1,1 dimethylethyl)oxy]carbonyl}(methyl)hydrazono]butanoyl}-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (0.5 g) (intermediate 2) in dichloromethane (5 ml) was added dropwise to trifluoroacetic acid (10 ml) under vigorous stirring. After 1 h the reaction mixture was concentrated in vacuo and sodium hydroxide (1N) was added until pH ˜12, then the mixture was extracted twice with dichloromethane. The organic phase was dried with sodium sulphate and evaporated to give the title compound (0.26 g).

Workup

  1. concentrationAfter 1 h the reaction mixture was concentrated in vacuo and sodium hydroxide (1N)
  2. additionwas added until pH ˜12
  3. extractionthe mixture was extracted twice with dichloromethane
  4. dry with materialThe organic phase was dried with sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-19d5bc8b25c84dd5ad80e69e3069abd0
Source dataset
uspto-grants-2011_08
Patent number
US08003638B2

Reaction notes

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