Water → 1,1-dimethylethyl 7-[5-acetyl-2-({[4-(ethyloxy)-2-pyridinyl]methyl}oxy)phenyl]-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

HRID 880000Notes

Reaction equation

HRID 880000 reaction equation
[CH3:1][C:2](C)([O-:4])C.[K+].[C:7]([C:10]1[CH:11]=[CH:12][C:13]([O:34][CH2:35][C:36]2[CH:41]=[C:40](Cl)[CH:39]=[CH:38][N:37]=2)=[C:14]([C:16]2[CH:33]=[CH:32][C:19]3[CH2:20][CH2:21][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:23][CH2:24][C:18]=3[CH:17]=2)[CH:15]=1)(=[O:9])[CH3:8].O>C(O)C>[C:7]([C:10]1[CH:11]=[CH:12][C:13]([O:34][CH2:35][C:36]2[CH:41]=[C:40]([O:4][CH2:2][CH3:1])[CH:39]=[CH:38][N:37]=2)=[C:14]([C:16]2[CH:33]=[CH:32][C:19]3[CH2:20][CH2:21][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:23][CH2:24][C:18]=3[CH:17]=2)[CH:15]=1)(=[O:9])[CH3:8]

Participants

5

Reactant 3

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 706649001,1-dimethylethyl 7-(5-acetyl-2-{[(4-chloro-2-pyridinyl)methyl]oxy}phenyl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

Product 1

HCID 706653891,1-dimethylethyl 7-[5-acetyl-2-({[4-(ethyloxy)-2-pyridinyl]methyl}oxy)phenyl]-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Potassium tert-butoxide (0.132 g) in ethanol (4 ml) was stirred for 15 min before adding 1,1-dimethylethyl 7-(5-acetyl-2-{[(4-chloro-2-pyridinyl)methyl]oxy}phenyl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate, (0.4 g) and this was heated in a microwave at 110 C for 1.5 h. Water (20 ml) was added to the cooled mixture and this was extracted with DCM (2×30 ml). The combined organics were washed with brine, dried over sodium sulphate and concentrated in vacuo. The crude product was purified through silica eluting with 0-45% ethyl acetate in hexane to give the title compound, 0.16 g

Workup

  1. temperaturethis was heated in a microwave at 110 C for 1.5 h
  2. extractionthis was extracted with DCM (2×30 ml)
  3. washThe combined organics were washed with brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified through silica eluting with 0-45% ethyl acetate in hexane

Sources & evidence

ORD record
ord-d069fd402d9b4d918452211ce1501fa0
Source dataset
uspto-grants-2015_03
Patent number
US08993560B2

Reaction notes

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