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

HRID 1674751Notes

Reaction equation

HRID 1674751 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-74ab97140fcb42ce8b49852dd031078f
Source dataset
uspto-grants-2011_08
Patent number
US08003641B2

Reaction notes

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