3-Fluorobenzylamine → N-(3-Fluoro-benzyl)-2-(2-fluoro-biphenyl-4-yl)-acetamide

HRID 1674745Notes

Reaction equation

HRID 1674745 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]([OH:11])=O)[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[F:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22][NH2:23].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>[F:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22][NH:23][C:9](=[O:11])[CH2:8][C:6]1[CH:5]=[CH:4][C:3]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:2]([F:1])[CH:7]=1

Participants

7

Reactant 4

HCID 668533-FluorobenzylamineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 118312372-(2-Fluoro-(1,1'-biphenyl)-4-yl)acetic acid

Product 1

HCID 11580859N-(3-Fluoro-benzyl)-2-(2-fluoro-biphenyl-4-yl)-acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(2-Fluoro-biphenyl-4-yl)-acetic acid (0.12 gm, 0.5 mmole), 3-fluorobenzylamine (0.0.8 ml, 0.6 mmole), PyBOP (0.34 gm, 0.6 mmole), and DIEA (0.22 ml, 1.3 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. (0.140 gm, 83%); H1-NMR INOVA-500 (DMSO d6) δ 3.580 (s, 2H), 4.316 (d, J=5.5 Hz, 2H), 7.037-7.110 (m, 3H), 7.210-7.247 (m, 2H), 7.343-7.372 (m, 2H), 7.457-7.501 (m, 3H), 7.544 (d, J=8.0 Hz, 2H), 8.660 (t, J=6.0 Hz, 1H). MS (m/z) 338.1 (M+H)+.

Workup

  1. filtrationwas collected by filtration
  2. customre-crystallized

Sources & evidence

ORD record
ord-19d48ef9163f4965baa53e299daf02db
Source dataset
uspto-grants-2011_08
Patent number
US08003641B2

Reaction notes

Loading…