2-Chloro-4-fluorophenol → Methyl 4-[(1S)-1-({[5-chloro-2-(2-chloro-4-fluorophenoxy)pyridin-3-yl]carbonyl}amino)ethyl]benzoate

HRID 1293194Notes

Reaction equation

HRID 1293194 reaction equation
Cl[C:2]1[C:7]([C:8]([NH:10][C@H:11]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=2)[CH3:12])=[O:9])=[CH:6][C:5]([Cl:23])=[CH:4][N:3]=1.[Cl:24][C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=1[OH:32]>>[Cl:23][C:5]1[CH:6]=[C:7]([C:8]([NH:10][C@H:11]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=2)[CH3:12])=[O:9])[C:2]([O:32][C:26]2[CH:27]=[CH:28][C:29]([F:31])=[CH:30][C:25]=2[Cl:24])=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 748142-Chloro-4-fluorophenolHCID 86601543Methyl 4-((1S)-1-{[(2,5-dichloropyridin-3-yl)carbonyl]amino}ethyl)benzoate

Product 1

HCID 69415978Methyl 4-[(1S)-1-({[5-chloro-2-(2-chloro-4-fluorophenoxy)pyridin-3-yl]carbonyl}amino)ethyl]benzoate

Procedure

The title compound was prepared according to the procedure described in step 2 of Example 48 from methyl 4-((1S)-1-{[(2,5-dichloropyridin-3-yl)carbonyl]amino}ethyl)benzoate (step 1 of Example 48) and 2-chloro-4-fluorophenol: 1H-NMR (CDCl3) δ 8.54 (1H, d, J=2.6 Hz), 8,12 (1H, br.s), 8.09 (1H, d, J=2.6 Hz), 8.04–7.98 (2H, m), 7.48–7.41 (2H, m), 7.32–7.25 (2H, m), 7.15–7.07 (1H, m), 5.45–5.33 (1H, m), 3.90 (3H, s), 1.61 (3H, d, J=7.0 Hz); MS (ESI) m/z 463 (M+H)+, 461 (M−H)−.

Sources & evidence

ORD record
ord-6d1e75f3123f418c9244e191f946b59d
Source dataset
uspto-grants-2007_07
Patent number
US07238714B2

Reaction notes

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