2-amino-N-(2,4-dimethyl-3-(((2-methoxy-1-(pyridin-2-ylmethyl)-1H-benzo[d]imidazol-4-yl)oxy)methyl)phenyl)-N-methylacetamide → N-(2-((3-(((2-methoxy-1-(pyridin-2-ylmethyl)-1H-benzo[d]imidazol-4-yl)oxy)methyl)-2,4-dimethylphenyl)(methyl)amino)-2-oxoethyl)-3-(2-oxo-2,3-dihydrooxazolo[4,5-b]pyridin-6-yl)propanamide

HRID 889173Notes

Reaction equation

HRID 889173 reaction equation
[NH2:1][CH2:2][C:3]([N:5]([C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]([CH2:14][O:15][C:16]2[C:24]3[N:23]=[C:22]([O:25][CH3:26])[N:21]([CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=4)[C:20]=3[CH:19]=[CH:18][CH:17]=2)[C:8]=1[CH3:34])[CH3:6])=[O:4].[O:35]=[C:36]1[NH:49][C:39]2=[N:40][CH:41]=[C:42]([CH2:44][CH2:45][C:46](O)=[O:47])[CH:43]=[C:38]2[O:37]1.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>>[CH3:26][O:25][C:22]1[N:21]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([O:15][CH2:14][C:9]3[C:8]([CH3:34])=[C:7]([N:5]([CH3:6])[C:3](=[O:4])[CH2:2][NH:1][C:46](=[O:47])[CH2:45][CH2:44][C:42]4[CH:43]=[C:38]5[O:37][C:36](=[O:35])[NH:49][C:39]5=[N:40][CH:41]=4)[CH:12]=[CH:11][C:10]=3[CH3:13])[C:24]=2[N:23]=1

Participants

4

Reactant 3

HCID 667599582-amino-N-(2,4-dimethyl-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)benzamideHCID 667611473-(2-Oxo-2,3-dihydrooxazolo[4,5-b]pyridin-6-yl)propanoic acid

Product 1

HCID 66760605N-(2-((3-(((2-methoxy-1-(pyridin-2-ylmethyl)-1H-benzo[d]imidazol-4-yl)oxy)methyl)-2,4-dimethylphenyl)(methyl)amino)-2-oxoethyl)-3-(2-oxo-2,3-dihydrooxazolo[4,5-b]pyridin-6-yl)propanamide

Procedure

2-amino-N-(2,4-dimethyl-3-(((2-methoxy-1-(pyridin-2-ylmethyl)-1H-benzo[d]imidazol-4-yl)oxy)methyl)phenyl)-N-methylacetamide and 3-(2-oxo-2,3-dihydrooxazolo[4,5-b]pyridin-6-yl)propanoic acid were used to prepare 3 as described above for compound 1. LCMS (+APCI) 650 (M+). 1H-NMR (CDCl3, δ ppm): 8.59 (m, 1H), 7.85 (d, J=2.0 Hz, 1H), 7.60 (dt, J=2.0, 7.6 Hz, 1H), 7.22 (m, 2H), 7.05 (t, J=8.0 Hz, 1H), 6.95 (d, J=7.6 Hz, 1H), 6.90 (d, J=8.0 Hz, 1H), 6.82 (m, 3H), 6.73 (bt, 1H), 5.30 (m, 4H), 4.21 (s, 3H), 3.72 (dd, 4.0, 18.0 Hz, 1H), 3.44 (dd, J=4.4, 18.0 Hz, 1H), 3.25 (s, 3H), 2.95 (m, 2H), 2.56 (m, 2H), 2.33 (s, 3H), 2.27 (s, 3H). Calcd. for C35H35N7O6+0.3H2O: C, 64.17; H, 5.48; N, 14.97. Found: C, 64.06; H, 5.46; N, 14.96.

Workup

  1. customto prepare 3

Sources & evidence

ORD record
ord-852f2367a6e14cfe9edf7eb51d9f5670
Source dataset
uspto-grants-2012_08
Patent number
US08252793B2

Reaction notes

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