Hordenine → HCID 69417244, compound

HRID 1293250Notes

Reaction equation

HRID 1293250 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.[CH3:24][N:25]([CH3:35])[CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1>>[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:34][C:31]2[CH:30]=[CH:29][C:28]([CH2:27][CH2:26][N:25]([CH3:24])[CH3:35])=[CH:33][CH:32]=2)=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 68313HordenineHCID 86601543Methyl 4-((1S)-1-{[(2,5-dichloropyridin-3-yl)carbonyl]amino}ethyl)benzoate

Product 1

HCID 69417244HCID 69417244, compound

Procedure

The title compound was prepared according to the procedure described in step 2 of Example 45 from methyl 4-((1S)-1-{[(2,5-dichloropyridin-3-yl)carbonyl]amino}ethyl)benzoate (step 1 of Example 48) and 4-[2-(dimethylamino)ethyl]phenol: 1H-NMR (CDCl3) δ 8.53 (1H, d, J=2.6 Hz), 8.23 (1H, d, J=7.5 Hz), 8.13 (1H, d, J=2.8 Hz), 8.02–7.98 (2H, m), 7.43 (2H, d, J=8.3 Hz), 7.33–7.30 (2H, m), 7.11–7.06 (2H, m), 5.39–5.30 (1H, m), 3.90 (3H, s), 2.87–2.82 (2H, m), 2.63–2.58 (2H, m), 2.33 (6H, s), 1.59 (3H, d, J=7.0 Hz).

Sources & evidence

ORD record
ord-89ce5868f69c403ab29fd661eececaa7
Source dataset
uspto-grants-2007_07
Patent number
US07238714B2

Reaction notes

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