3-Fluorobenzylamine → 2-(6-Chloro-pyridin-3-yl)-N-(3-fluoro-benzyl)-acetamide

HRID 2427451Notes

Reaction equation

HRID 2427451 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][N:3]=1.[F:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH2:16][NH2:17].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][C:9]([NH:17][CH2:16][C:15]2[CH:18]=[CH:19][CH:20]=[C:13]([F:12])[CH:14]=2)=[O:11])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 668533-FluorobenzylamineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 140715712-(6-Chloropyridin-3-yl)acetic acid

Product 1

HCID 862487322-(6-Chloro-pyridin-3-yl)-N-(3-fluoro-benzyl)-acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-chloropyridine-5-acetic acid (0.2 gm, 1.21 mmole), 3-fluorobenzylamine (0.15 ml, 1.2 mmole), PyBOP (0.67 gm, 1.3 mmole), and DIEA (0.43 ml, 2.6 mmole) was dissolved in DMF stirred overnight, the reaction mixture was then poured into water, solid was collected by filtration, re-crystallized using water-methanol (0.3 gm, 85%); H1-NMR INOVA-500 (CDCl3) δ 3.562 (s, 2H), 4.429 (d, J=6.5 Hz, 2H), 5.868 (s, 1H), 6.929-7.015 (m, 3H), 7.300-7.333 (m, 2H), 7.668 (dd, J=8, 2.5 Hz, 1H), 8.280 (d, J=2.5 Hz, 1H).

Workup

  1. filtrationwas collected by filtration
  2. customre-crystallized

Sources & evidence

ORD record
ord-71004bb9379d48349b436a13bbaaa2ec
Source dataset
uspto-grants-2011_06
Patent number
US07968574B2

Reaction notes

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