Diethyl (4-{[4-chloro-5-(trifluoromethyl) pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate → HCID 178476792, compound

HRID 511238Notes

Reaction equation

HRID 511238 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:27]=[CH:26][C:16](CP(=O)(OCC)OCC)=[CH:15][C:14]=2OC)[N:3]=1.NC1C=CC([CH2:35][CH2:36][PH:37](=[O:41])[O:38][CH2:39][CH3:40])=CC=1>>[Cl:1][C:2]1[C:7]([C:8]([F:10])([F:9])[F:11])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:27]=[CH:26][C:16]([CH2:35][CH2:36][PH:37](=[O:41])[O:38][CH2:39][CH3:40])=[CH:15][CH:14]=2)[N:3]=1

Participants

3

Reactant 2

HCID 86654002Diethyl (4-{[4-chloro-5-(trifluoromethyl) pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonateHCID 178476796HCID 178476796, compound

Product 1

HCID 178476792HCID 178476792, compoundYield 61%

Procedure

Prepared as described above for diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate using ethyl (4-aminobenzyl)methylphosphinate in place of diethyl (4-amino-3-methoxybenzyl)phosphonate. Following chromatography, the semi-pure product was crystallized from ethyl acetate to afford 1.1 g (61% yield) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.64 (s, 1H), 8.79 (d, J=0.51 Hz, 1H), 7.62 (d, J=8.34 Hz, 2H), 7.25 (dd, J=2.27, 8.59 Hz, 2H), 3.86-4.01 (m, 2H), 3.15 (d, J=17.68 Hz, 2H), 1.31 (d, J=13.64 Hz, 3H), 1.19 (t, J=6.95 Hz, 3H); MS (ES+): m/z: 396.0708 [MH+]. HPLC: tR=1.41 min (UPLC TOF MS: polar—3 min).

Workup

  1. customPrepared
  2. customthe semi-pure product was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-cad2b028327145bfa9683ac5e79b587d
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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