3-(4-(Methylcarbamoyl)phenyl)propanoic acid → 4-(3-((2-((2,4-dichloro-3-(((2-methoxy-1-(pyridin-2-ylmethyl)-1H-benzo[d]imidazol-4-yl)oxy)methyl)phenyl)(methyl)amino)-2-oxoethyl)amino)-3-oxopropyl)-N-methylbenzamide

HRID 889197Notes

Reaction equation

HRID 889197 reaction equation
CNC(C1C=CC(CCC(O)=O)=CC=1)=O.NCC(N(C1C=CC(Cl)=C(COC2C3N=C(OC)N(CC4C=CC=CN=4)C=3C=CC=2)C=1Cl)C)=O.[Cl:50][C:51]1[C:56]([CH2:57][O:58][C:59]2[C:67]3[N:66]=[C:65]([O:68][CH3:69])[N:64]([CH2:70][C:71]4[CH:76]=[CH:75][CH:74]=[CH:73][N:72]=4)[C:63]=3[CH:62]=[CH:61][CH:60]=2)=[C:55]([Cl:77])[CH:54]=[CH:53][C:52]=1[N:78]([CH3:100])[C:79](=[O:99])[CH2:80][NH:81][C:82](=[O:98])[CH2:83][CH2:84][C:85]1[CH:97]=[CH:96][C:88]([C:89]([NH:91][CH2:92]COC)=[O:90])=[CH:87][CH:86]=1>>[Cl:50][C:51]1[C:56]([CH2:57][O:58][C:59]2[C:67]3[N:66]=[C:65]([O:68][CH3:69])[N:64]([CH2:70][C:71]4[CH:76]=[CH:75][CH:74]=[CH:73][N:72]=4)[C:63]=3[CH:62]=[CH:61][CH:60]=2)=[C:55]([Cl:77])[CH:54]=[CH:53][C:52]=1[N:78]([CH3:100])[C:79](=[O:99])[CH2:80][NH:81][C:82](=[O:98])[CH2:83][CH2:84][C:85]1[CH:86]=[CH:87][C:88]([C:89]([NH:91][CH3:92])=[O:90])=[CH:96][CH:97]=1

Participants

4

Reactant 3

HCID 196034293-(4-(Methylcarbamoyl)phenyl)propanoic acidHCID 667603852-amino-N-(2,4-dichloro-3-(((2-methoxy-1-(pyridin-2-ylmethyl)-1H-benzo[d]imidazol-4-yl)oxy)methyl)phenyl)-N-methylacetamideHCID 667609784-(3-((2-((2,4-dichloro-3-(((2-methoxy-1-(pyridin-2-ylmethyl)-1H-benzo[d]imidazol-4-yl)oxy)methyl)phenyl)(methyl)amino)-2-oxoethyl)amino)-3-oxopropyl)-N-(2-methoxyethyl)benzamide

Product 1

HCID 568397914-(3-((2-((2,4-dichloro-3-(((2-methoxy-1-(pyridin-2-ylmethyl)-1H-benzo[d]imidazol-4-yl)oxy)methyl)phenyl)(methyl)amino)-2-oxoethyl)amino)-3-oxopropyl)-N-methylbenzamide

Procedure

Compound 33 is prepared from 3-(4-(methylcarbamoyl)phenyl)propanoic acid and 2-amino-N-(2,4-dichloro-3-(((2-methoxy-1-(pyridin-2-ylmethyl)-1H-benzo[d]imidazol-4-yl)oxy)methyl)phenyl)-N-methylacetamide as described for compound 1. MS (ESI) 689 (M+) 1HNMR (CDCl3), 2.42-2.58 (m, 2H), 2.80-2.90 (m, 5H), 3.18 (s, 3H), 3.3-3.5 (m, 1H), 3.65-3.72 (m, 1H), 4.14 (s, 3H), 5.25 (s, 2H), 5.5-5.7 (m, 2H), 6.4-6.6 (m, 2H), 6.75-6.82 (m, 2H), 6.85-6.91 (m, 1H), 6.95-7.10 (m, 3H), 7.38-7.45 (m, 1H), 7.52-7.62 (m, 1H), 6.8-6.72 (m, 2H), 8.52-8.60 (m, 1H).

Sources & evidence

ORD record
ord-a8d2c8583dbd498e804865732df30e75
Source dataset
uspto-grants-2012_08
Patent number
US08252793B2

Reaction notes

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