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

HRID 1594141Notes

Reaction equation

HRID 1594141 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-25acc278a5884c0983b794451489c5e0
Source dataset
uspto-grants-2007_11
Patent number
US07300931B2

Reaction notes

Loading…