Benzylamine → HCID 178522832, compound

HRID 523384Notes

Reaction equation

HRID 523384 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:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[CH2:30][NH:37][C:27]([C:26]1[C:20]2[NH:19][C:18]([C:12]3[C:13](=[O:17])[NH:14][CH:15]=[CH:16][C:11]=3[NH:10][CH2:9][CH2:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)=[N:22][C:21]=2[CH:23]=[CH:24][CH:25]=1)=[O:28]

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 178522832HCID 178522832, compound

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 2-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 2-fluoro-benzylamide. LC/MS calcd for C28H23ClFN5O2 (m/e) 515.0, obsd 516 (M+H). 1H NMR (tautomers, DMSO-d6) δ: 13.33-13.49 (m, 1H), 11.14-11.45 (m, 1H), 10.05-10.92 (m, 1H), 9.08-9.32 (m, 1H), 7.70-7.98 (m, 2H), 7.02-7.61 (m, 11H), 6.16-6.32 (m, 1H), 4.53-4.80 (m, 2H), 3.43-3.84 (m, 2H), 2.75-3.12 (m, 2H).

Sources & evidence

ORD record
ord-7fd2590c785147be9ba6f1832d6a725f
Source dataset
uspto-grants-2016_05
Patent number
US09334480B2

Reaction notes

Loading…