HCID 66760518, compound → HCID 66760409, compound

HRID 889224Notes

Reaction equation

HRID 889224 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][C:14]2[N:15]=[CH:16][N:17]([CH3:19])[CH:18]=2)[C:9]2[C:4](=[C:5]([OH:20])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[Cl:21][C:22]1[C:27]([CH2:28]Cl)=[C:26]([Cl:30])[CH:25]=[CH:24][C:23]=1[N:31]([CH3:50])[C:32](=[O:49])[CH2:33][NH:34][C:35](=[O:48])[CH2:36][CH2:37][C:38]1[CH:39]=[CH:40][C:41]([C:44]([NH:46][CH3:47])=[O:45])=[N:42][CH:43]=1.[CH3:51][C:52]1[CH:61]=[C:60]([O:62][CH2:63][C:64]2[N:65]([CH3:69])[CH:66]=[CH:67][N:68]=2)[C:59]2[C:54](=[C:55]([OH:70])[CH:56]=[CH:57][CH:58]=2)[N:53]=1>>[Cl:21][C:22]1[C:27]([CH2:28][O:20][C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[N:3]=[C:2]([CH3:1])[CH:11]=[C:10]3[O:12][CH2:13][C:14]2[N:15]=[CH:16][N:17]([CH3:19])[CH:18]=2)=[C:26]([Cl:30])[CH:25]=[CH:24][C:23]=1[N:31]([CH3:50])[C:32](=[O:49])[CH2:33][NH:34][C:35](=[O:48])[CH2:36][CH2:37][C:38]1[CH:39]=[CH:40][C:41]([C:44]([NH:46][CH3:47])=[O:45])=[N:42][CH:43]=1.[Cl:21][C:22]1[C:27]([CH2:28][O:70][C:55]2[CH:56]=[CH:57][CH:58]=[C:59]3[C:54]=2[N:53]=[C:52]([CH3:51])[CH:61]=[C:60]3[O:62][CH2:63][C:64]2[N:65]([CH3:69])[CH:66]=[CH:67][N:68]=2)=[C:26]([Cl:30])[CH:25]=[CH:24][C:23]=1[N:31]([CH3:50])[C:32](=[O:49])[CH2:33][NH:34][C:35](=[O:48])[CH2:36][CH2:37][C:38]1[CH:39]=[CH:40][C:41]([C:44]([NH:46][CH3:47])=[O:45])=[CH:1][CH:43]=1

Participants

5

Reactant 3

HCID 66760518HCID 66760518, compoundHCID 66760730HCID 66760730, compoundHCID 66761194HCID 66761194, compound2×

Product 2

HCID 66760409HCID 66760409, compoundHCID 66760643HCID 66760643, compound

Procedure

5-(3-((2-((2,4-dichloro-3-(((2-methyl-4-((1-methyl-1H-imidazol-4-yl)methoxy)quinolin-8-yl)oxy)methyl)phenyl)(methyl)amino)-2-oxoethyl)amino)-3-oxopropyl)-N-methylpicolinamide was prepared from 2-methyl-4-((1-methyl-1H-imidazol-4-yl)methoxy)quinolin-8-ol and 5-(3-((2-((2,4-dichloro-3-(chloromethyl)phenyl)(methyl)amino)-2-oxoethyl)amino)-3-oxopropyl)-N-methylpicolinamide as previously described. MS (+ESI) 704 (M+1). 1H-NMR (CDCl3, δ ppm): 8.36 (s, 1H), 8.08 (d, J=8.0 Hz, 1H), 7.94 (bs, 1H), 7.98 (dd, J=1.2, 9.2 Hz, 1H), 7.64 (dd, J=2.4, 8.4 Hz, 1H), 7.44 (m, 2H), 7.25 (m, 3H), 7.02 (s, 1H), 6.82 (s, 1H), 6.49 (bt, 1H), 5.61 (s, 2H), 5.22 (s, 2H), 3.75 (dd, 1H), 3.71 (s, 3H), 3.38 (dd, J=4, 17.6 Hz, 1H), 3.20 (s, 3H), 3.01 (d, J=5.2 Hz, 3H), 2.99 (m, 2H), 2.67 (s, 3H), 2.54 (t, J=7.6 Hz, 2H). 4-(3-((2-((2,4-dichloro-3-(((2-methyl-4-((1-methyl-1H-imidazol-2-yl)methoxy)quinolin-8-yl)oxy)methyl)phenyl)(methyl)amino)-2-oxoethyl)amino)-3-oxopropyl)-N-methylbenzamide was prepared from 2-methyl-4-((1-methyl-1H-imidazol-2-yl)methoxy)quinolin-8-ol and 5-(3-((2-((2,4-dichloro-3-(chloromethyl)phenyl)(methyl)amino)-2-oxoethyl)amino)-3-oxopropyl)-N-methylpicolinamide as previously described. LCMS (+ESI) 704 (M+).

Sources & evidence

ORD record
ord-445d1e09b3354880b1f5f4317882b583
Source dataset
uspto-grants-2012_08
Patent number
US08252793B2

Reaction notes

Loading…