3-(4-Acetamidophenyl)propanoic acid → 3-(4-acetamidophenyl)-N-(2-((2,4-dichloro-3-(((2-methyl-4-(pyridin-2-ylmethoxy)quinolin-8-yl)oxy)methyl)phenyl)(methyl)amino)-2-oxoethyl)propanamide

HRID 889193Notes

Reaction equation

[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13]([OH:15])=O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[NH2:16][CH2:17][C:18]([N:20]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([CH2:29][O:30][C:31]2[CH:32]=[CH:33][CH:34]=[C:35]3[C:40]=2[N:39]=[C:38]([CH3:41])[CH:37]=[C:36]3[O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=2)[C:23]=1[Cl:50])[CH3:21])=[O:19].ClC1C(COC2C3N=C(OC)N(CC4C=CC=CN=4)C=3C=CC=2)=C(Cl)C=CC=1N(C)C(=O)CNC(=O)CCC1C=CC(C(NCCOC)=O)=CC=1>>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH2:12][C:13]([NH:16][CH2:17][C:18]([N:20]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([CH2:29][O:30][C:31]3[CH:32]=[CH:33][CH:34]=[C:35]4[C:40]=3[N:39]=[C:38]([CH3:41])[CH:37]=[C:36]4[O:42][CH2:43][C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=3)[C:23]=2[Cl:50])[CH3:21])=[O:19])=[O:15])=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

Reactant 3

HCID 2329113-(4-Acetamidophenyl)propanoic acid

HCID 232920198-[3-(N-glycyl-N-methylamino)-2,6-dichlorobenzyloxy]-2-methyl-4-(2-pyridylmethoxy)quinoline

HCID 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 568397893-(4-acetamidophenyl)-N-(2-((2,4-dichloro-3-(((2-methyl-4-(pyridin-2-ylmethoxy)quinolin-8-yl)oxy)methyl)phenyl)(methyl)amino)-2-oxoethyl)propanamide

Procedure

Compound 28 was prepared from 3-(4-acetamidophenyl)propanoic acid and 2-amino-N-(2,4-dichloro-3-(((2-methyl-4-(pyridin-2-ylmethoxy)quinolin-8-yl)oxy)methyl)phenyl)-N-methylacetamide in a as described for compound 1. MS (APCI) 700(M+), 1H NMR (CDCl3) 1.91 (s, 3H), 2.4-2.6 (m, 5H), 2.80-2.93 (m, 2H), 3.10 (s, 3H), 3.32-3.45 (m, 1H), 3.61-3.71 (m, 1H), 5.41 (s, 2H), 5.45-5.56 (m, 2H), 6.41-6.45 (m, 1H), 6.71 (s, 1H), 6.91-7.05 (m, 3H), 7.18-7.21 (m, 1H), 7.22-7.28 (m, 1H), 7.31-7.50 (m, 2H), 7.55-7.60 (m, 1H), 7.65-7.75 (m, 1H), 7.91-7.99 (m, 1H), 8.61-8.69 (m, 1H), 9.14 (s, 1H).

Sources & evidence

ORD record: ord-693caf9f6a264704b2c92870db4a8a28
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252793B2

Reaction notes

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