Diethyl 3-chloro-4-aminobenzylphosphonate → Diethyl (3-chloro-4-{[4-{[2-(methylcarbamoyl)phenyl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate

HRID 1947855Notes

Reaction equation

HRID 1947855 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([NH:13][CH3:14])=[O:12])[C:5]([C:19]([F:22])([F:21])[F:20])=[CH:4][N:3]=1.[NH2:23][C:24]1[CH:38]=[CH:37][C:27]([CH2:28][P:29](=[O:36])([O:33][CH2:34][CH3:35])[O:30][CH2:31][CH3:32])=[CH:26][C:25]=1[Cl:39]>>[Cl:39][C:25]1[CH:26]=[C:27]([CH:37]=[CH:38][C:24]=1[NH:23][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11](=[O:12])[NH:13][CH3:14])[C:5]([C:19]([F:22])([F:21])[F:20])=[CH:4][N:3]=1)[CH2:28][P:29](=[O:36])([O:33][CH2:34][CH3:35])[O:30][CH2:31][CH3:32]

Participants

3

Reactant 2

HCID 19077629Diethyl 3-chloro-4-aminobenzylphosphonate2×HCID 866338612-((2-Chloro-5-(trifluoromethyl)pyrimidin-4-yl)amino)-N-methylbenzamide

Product 1

HCID 49821188Diethyl (3-chloro-4-{[4-{[2-(methylcarbamoyl)phenyl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate

Procedure

The title compound was prepared using the procedure from Example 102 with 2-{[2-chloro-5-(trifluoromethyl)pyrimidin-4-yl]amino}-N-methylbenzamide (0.060 g, 0.18 mmol) and diethyl (4-amino-3-chlorobenzyl)phosphonate (Compound 104A, 0.101 g, 0.363 mmol). 1H NMR (400 MHz, DMSO-d6) δ11.56 (s, 1H), 9.40 (s, 1H), 8.70 (d, J=4.55 Hz, 1H), 8.38 (s, 1H), 7.66 (dd, J=1.39, 7.96 Hz, 1H), 7.50 (d, J=8.08 Hz, 1H), 7.46 (t, J=2.27 Hz, 1H), 7.29-7.34 (m, 1H), 7.24-7.29 (m, 2H), 7.04 (t, J=7.20 Hz, 1H), 3.94-4.05 (m, 4H), 2.77 (d, J=4.55 Hz, 3H), 1.19 (t, J=6.95 Hz, 6H); MS (ES+): m/z: 572.08 [MH+]. HPLC: tR=3.42 min (Micromass ZQ3: polar—5 min).

Workup

  1. customHPLC: tR=3.42 min (Micromass ZQ3: polar—5 min)

Sources & evidence

ORD record
ord-3a2f37135f28468daa6fd714f15b8c06
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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