Benzylamine → 2-{4-[2-(3-chloro-phenyl)-ethylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-3H-benzoimidazole-4-carboxylic acid 4-fluoro-benzylamide

HRID 711325Notes

Reaction equation

HRID 711325 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][NH:10][C:11]2[CH:16]=[CH:15][NH:14][C:13](=[O:17])[C:12]=2[C:18]2[NH:19][C:20]3[C:26]([C:27](O)=[O:28])=[CH:25][CH:24]=[CH:23][C:21]=3[N:22]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:30]([NH2:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.[F:64][P-](F)(F)(F)(F)F.FC1C=C(C=CC=1)CNC(C1C2NC(C3C(=O)NC=CC=3NC[C@@H](O)C3C=CC=CC=3)=NC=2C=CC=1)=O>CN(C=O)C>[F:64][C:34]1[CH:35]=[CH:36][C:31]([CH2:30][NH:37][C:27]([C:26]2[C:20]3[NH:19][C:18]([C:12]4[C:13](=[O:17])[NH:14][CH:15]=[CH:16][C:11]=4[NH:10][CH2:9][CH2:8][C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=4)=[N:22][C:21]=3[CH:23]=[CH:24][CH:25]=2)=[O:28])=[CH:32][CH:33]=1

Participants

7

Reactant 5

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178522847HCID 178522847, compoundHCID 178524246HCID 178524246, compound

Product 1

HCID 1785229922-{4-[2-(3-chloro-phenyl)-ethylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-3H-benzoimidazole-4-carboxylic acid 4-fluoro-benzylamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-{4-[2-(3-chloro-phenyl)-ethylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-3H-benzoimidazole-4-carboxylic acid 4-fluoro-benzylamide was synthesized from 2-{4-[2-(3-chloro-phenyl)-ethylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-3H-benzoimidazole-4-carboxylic acid, benzylamine, DIEA, HATU and DMF using a similar procedure as 2-[4-((S)-2-hydroxy-2-phenyl-ethylamino)-2-oxo-1,2-dihydro-pyridin-3-yl]-3H-benzoimidazole-4-carboxylic acid 3-fluoro-benzylamide yielding 2-{4-[2-(3-chloro-phenyl)-ethylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-3H-benzoimidazole-4-carboxylic acid 4-fluoro-benzylamide. LC/MS calcd for C28H23ClFN5O2 (m/e) 515.0, obsd 516 (M+H). 1H NMR (tautomers, DMSO-d6): 13.30-13.51 (m, 1H), 11.11-11.49 (m, 1H), 9.98-10.95 (m, 1H), 9.06-9.36 (m, 1H), 7.68-8.00 (m, 2H), 6.93-7.65 (m, 11H), 6.22 (d, J=7.3 Hz, 1H), 4.47-4.74 (m, 2H), 3.59-3.85 (m, 2H), 3.05 (t, J=6.9 Hz, 2H).

Sources & evidence

ORD record
ord-2256f5c119bd456a9be1dd178dc373f0
Source dataset
uspto-grants-2015_11
Patent number
US09181218B2

Reaction notes

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