Benzylamine → HCID 178522993, compound

HRID 523379Notes

Reaction equation

HRID 523379 reaction equation
[OH:1][C@@H:2]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:3][NH:4][C:5]1[CH:10]=[CH:9][NH:8][C:7](=[O:11])[C:6]=1[C:12]1[NH:13][C:14]2[C:20]([C:21]([OH:23])=O)=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=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:21]([C:20]2[C:14]3[NH:13][C:12]([C:6]4[C:7](=[O:11])[NH:8][CH:9]=[CH:10][C:5]=4[NH:4][CH2:3][C@@H:2]([OH:1])[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)=[N:16][C:15]=3[CH:17]=[CH:18][CH:19]=2)=[O:23])=[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 178524247HCID 178524247, compound

Product 1

HCID 178522993HCID 178522993, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-[4-((S)-2-Hydroxy-2-phenyl-ethylamino)-2-oxo-1,2-dihydro-pyridin-3-yl]-3H-benzoimidazole-4-carboxylic acid4-fluoro-benzylamide was synthesized from 2-[4-((S)-2-hydroxy-2-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-((S)-2-hydroxy-2-phenyl-ethylamino)-2-oxo-1,2-dihydro-pyridin-3-yl]-3H-benzoimidazole-4-carboxylic acid 4-fluoro-benzylamide. LC/MS calcd for C28H24FN5O3 (m/e) 497.0, obsd 498 (M+H). 1H NMR (DMSO-d6) δ: 13.35-13.53 (m, 1H), 11.13-11.38 (m, 1H), 10.35-11.03 (m, 1H), 9.19-9.42 (m, 1H), 7.68-7.97 (m, 2H), 7.24-7.58 (m, 9H), 7.08-7.22 (m, 2H), 6.13-6.30 (m, 1H), 5.74-6.02 (m, 1H), 4.49-4.98 (m, 3H), 3.49-3.29 (m, 2H).

Sources & evidence

ORD record
ord-653ecc40c64f42a29f6578742d15bc86
Source dataset
uspto-grants-2016_05
Patent number
US09334480B2

Reaction notes

Loading…