HCID 66760610, compound → HCID 66759342, compound

HRID 889223Notes

Reaction equation

HRID 889223 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][O:5][C:6]1[C:15]2[C:10](=[C:11]([OH:16])[CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([CH3:17])[CH:7]=1.[Cl:22][C:23]1[C:28]([CH2:29]Cl)=[C:27]([Cl:31])[CH:26]=[CH:25][C:24]=1[N:32]([CH3:51])[C:33](=[O:50])[CH2:34][NH:35][C:36](=[O:49])[CH2:37][CH2:38][C:39]1[CH:40]=[CH:41][C:42]([C:45]([NH:47][CH3:48])=[O:46])=[N:43][CH:44]=1>>[Cl:22][C:23]1[C:28]([CH2:29][O:16][C:11]2[CH:12]=[CH:13][CH:14]=[C:15]3[C:10]=2[N:9]=[C:8]([CH3:17])[CH:7]=[C:6]3[O:5][CH2:4][C:3]2[CH:18]=[CH:19][CH:20]=[CH:21][C:2]=2[F:1])=[C:27]([Cl:31])[CH:26]=[CH:25][C:24]=1[N:32]([CH3:51])[C:33](=[O:50])[CH2:34][NH:35][C:36](=[O:49])[CH2:37][CH2:38][C:39]1[CH:40]=[CH:41][C:42]([C:45]([NH:47][CH3:48])=[O:46])=[N:43][CH:44]=1

Participants

3

Reactant 2

HCID 66760610HCID 66760610, compoundHCID 66761194HCID 66761194, compound

Product 1

HCID 66759342HCID 66759342, compoundYield 53%

Procedure

4-((2-fluorobenzyl)oxy)-2-methylquinolin-8-ol from step 1 was reacted with 5-(3-((2-((2,4-dichloro-3-(chloromethyl)phenyl)(methyl)amino)-2-oxoethyl)amino)-3-oxopropyl)-N-methylpicolinamide as described previously to give 5-(3-((2-((2,4-dichloro-3-(((4-((2-fluorobenzyl)oxy)-2-methylquinolin-8-yl)oxy)methyl)phenyl)(methyl)amino)-2-oxoethyl)amino)-3-oxopropyl)-N-methylpicolinamide in 53% yield. MS (+APCI) 718 (M+). 1H-NMR (CDCl3, δ ppm): 8.36 (s, 1H), 8.07 (d, J=8.0 Hz, 1H), 7.95 (bd, 1H), 7.94 (d, J=8.0 Hz, 1H), 7.63 (m, 1H), 7.58 (m, 1H), 7.45 (d, J=8.4 Hz, 1H), 7.36 (t, J=8.0 Hz, 1H), 7.25 (m, 4H), 7.15 (m, 1H), 7.05 (m, 1H), 6.77 (bs, 1H), 6.40 (bt, 1H), 5.62 (s, 2H), 5.38 (s, 2H), 3.76 (dd, J=5.2, 17.6 Hz, 1H), 3.46 (dd, J=3.6, 18 Hz, 1H), 3.22 (s, 3H), 3.00 (m, 6H), 2.69 (m, 2H), 2.56 (t, 2).

Sources & evidence

ORD record
ord-e26c1bc4b2564c209a79e1bd185c71d1
Source dataset
uspto-grants-2012_08
Patent number
US08252793B2

Reaction notes

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