Trifluoroacetic acid → N-(4-(5-Chloropyrimidin-2-yl)benzyl)-5-((5-methylpyridin-2-yl)methoxy)-2-nitroaniline

HRID 1848721Notes

Reaction equation

HRID 1848721 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:22]=[CH:21][C:11]([CH2:12][NH:13][C:14](=O)OC(C)(C)C)=[CH:10][CH:9]=2)=[N:6][CH:7]=1.C(O)(C(F)(F)F)=O.CCN(C(C)C)C(C)C.F[C:40]1[CH:41]=[C:42]([CH:52]=C[C:54]=1[N+:55]([O-:57])=[O:56])[O:43][CH2:44][C:45]1[CH:50]=[CH:49][C:48]([CH3:51])=[CH:47][N:46]=1>C(Cl)Cl.O.CC(N(C)C)=O>[Cl:1][C:2]1[CH:7]=[N:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH2:12][NH:13][C:14]3[CH:52]=[C:42]([O:43][CH2:44][C:45]4[CH:50]=[CH:49][C:48]([CH3:51])=[CH:47][N:46]=4)[CH:41]=[CH:40][C:54]=3[N+:55]([O-:57])=[O:56])=[CH:21][CH:22]=2)=[N:4][CH:3]=1

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 90410805Tert-butyl 4-(5-chloropyrimidin-2-yl)benzylcarbamateHCID 904110842-((3-Fluoro-4-nitrophenoxy)methyl)-5-methylpyridine

Product 1

HCID 90411558N-(4-(5-Chloropyrimidin-2-yl)benzyl)-5-((5-methylpyridin-2-yl)methoxy)-2-nitroanilineYield 92.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of tert-butyl 4-(5-chloropyrimidin-2-yl)benzylcarbamate (355 mg, 1.11 mmol) in DCM (10 mL) was added TFA (1 mL). The reaction mixture was stirred for 5 h at RT and concentrated to dryness. To the resulting residue was added DMA (3 mL), DIPEA (0.57 mL) and 2-((3-fluoro-4-nitrophenoxy)methyl)-5-methylpyridine (0.29 g, 1.11 mmol). The mixture and heated to 80° Celsius for 6 h. The mixture was then poured into water and the solids were collected by filtration to provide of the title compound (475 mg). 1H NMR (400 MHz, CDCl3) δ 8.77-8.72 (s, 2H), 8.41-8.32 (m, 2H), 8.21-8.13 (d, J=9.5, 1H), 7.49-7.39 (m, 3H), 7.26-7.21 (m, 3H), 6.38-6.30 (dd, J=9.5, 2.5, 1H), 6.27-6.21 (d, J=2.5, 1H), 5.14-5.09 (s, 2H), 4.60-4.53 (d, J=5.8, 2H), 2.30-2.25 (s, 3H).

Workup

  1. concentrationconcentrated to dryness
  2. temperatureThe mixture and heated to 80° Celsius for 6 h
  3. filtrationthe solids were collected by filtration

Sources & evidence

ORD record
ord-fccd790b4149457390725ec7354343df
Source dataset
uspto-grants-2015_02
Patent number
US08952177B2

Reaction notes

Loading…