4-(Pyridin-2-yl)phenol → tert-Butyl 4-[(1S)-1-({[5-chloro-2-(4-pyridin-2-ylphenoxy)pyridin-3-yl]carbonyl}amino)ethyl]benzoate

HRID 1293322Notes

Reaction equation

HRID 1293322 reaction equation
Cl[C:2]1[C:7]([C:8]([NH:10][C@H:11]([C:13]2[CH:25]=[CH:24][C:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:15][CH:14]=2)[CH3:12])=[O:9])=[CH:6][C:5]([Cl:26])=[CH:4][N:3]=1.[N:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=1>>[Cl:26][C:5]1[CH:6]=[C:7]([C:8]([NH:10][C@H:11]([C:13]2[CH:25]=[CH:24][C:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:15][CH:14]=2)[CH3:12])=[O:9])[C:2]([O:39][C:36]2[CH:35]=[CH:34][C:33]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][N:27]=3)=[CH:38][CH:37]=2)=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 4594994-(Pyridin-2-yl)phenolHCID 57572256tert-butyl 4-((1S)-1-{[(2,5-dichloropyridin-3-yl)carbonyl]amino}ethyl)benzoate

Product 1

HCID 69417723tert-Butyl 4-[(1S)-1-({[5-chloro-2-(4-pyridin-2-ylphenoxy)pyridin-3-yl]carbonyl}amino)ethyl]benzoate

Procedure

The title compound was prepared according to the procedure described in step 2 of Example 45 from tert-butyl 4-((1S)-1-{[(2,5-dichloropyridin-3-yl)carbonyl]amino}ethyl)benzoate (step 1 of Example 45) and 4-pyridin-2-ylphenol (Tetrahedron, 1998, 54, 1289): 1H-NMR (CDCl3) δ 8.71 (1H, m), 8.56 (1H, d, J=2.8 Hz), 8.19–7.71 (8H, m), 7.41 (2H, d, J=1.8 Hz), 7.29–7.25 (3H, m), 5.36 (1H, m), 1.58 (3H, d, J=7.0 Hz), 1.57 (9H, s).

Sources & evidence

ORD record
ord-21e9cfe883ea42aa83a9c534061259f8
Source dataset
uspto-grants-2007_07
Patent number
US07238714B2

Reaction notes

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