6-(Methylamino)-2-pyridylethanol → methyl (S)-8-[2-[6-(methylamino)pyridin-2-yl]-1-ethoxy]-3-oxo-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetate

HRID 2416743Notes

Reaction equation

HRID 2416743 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[C:7]([CH:9](O)[CH3:10])[CH:6]=[CH:5][CH:4]=1.[OH:12][C:13]1[CH:33]=[CH:32][C:16]2[CH2:17][C@@H:18]([CH2:28][C:29]([O-:31])=[O:30])[C:19](=[O:27])[N:20]([CH2:22][C:23]([F:26])([F:25])[F:24])[CH2:21][C:15]=2[CH:14]=1.O[C:35]1C=CC2C[C@H](CC([O-])=O)C(=O)N(CC(F)(F)F)CC=2C=1>>[CH3:1][NH:2][C:3]1[N:8]=[C:7]([CH2:9][CH2:10][O:12][C:13]2[CH:33]=[CH:32][C:16]3[CH2:17][C@@H:18]([CH2:28][C:29]([O:31][CH3:35])=[O:30])[C:19](=[O:27])[N:20]([CH2:22][C:23]([F:26])([F:24])[F:25])[CH2:21][C:15]=3[CH:14]=2)[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 223194656-(Methylamino)-2-pyridylethanolHCID 57459733(S)-8-hydroxy-3-oxo-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetateHCID 57459734(R)-8-hydroxy-3-oxo-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetate

Product 1

HCID 10718986methyl (S)-8-[2-[6-(methylamino)pyridin-2-yl]-1-ethoxy]-3-oxo-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetate

Procedure

According to the method of Example 37(a), except substituting 6-(methylamino)-2-pyridylethanol for the 2-[(3-hydroxy-1H-propyl)amino]pyridine-N-oxide, and substituting (S)-8-hydroxy-3-oxo-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetate for the (R)-8-hydroxy-3-oxo-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetate, the title compound was prepared as a colorless oil: MS (ES) m/e 466.2 (M+H)+.

Sources & evidence

ORD record
ord-26b00a441e1e43499c240f438c38e432
Source dataset
uspto-grants-2004_11
Patent number
US06825188B2

Reaction notes

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