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

HRID 1907919Notes

Reaction equation

HRID 1907919 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-15bec04b9d3745e8b0488e78daaa2a15
Source dataset
uspto-grants-2013_12
Patent number
US08598169B2

Reaction notes

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