2-((2-Chloro-5-(trifluoromethyl)pyrimidin-4-yl)amino)-N-methylbenzamide → Bis(2-methoxyethyl) (3-methoxy-4-{[4-{[2-(methylcarbamoyl)phenyl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate

HRID 1948027Notes

Reaction equation

HRID 1948027 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.[CH3:23][O:24][CH2:25][CH2:26][O:27][P:28]([CH2:35][C:36]1[CH:41]=[CH:40][C:39]([NH2:42])=[C:38]([O:43][CH3:44])[CH:37]=1)(=[O:34])[O:29][CH2:30][CH2:31][O:32][CH3:33]>>[CH3:33][O:32][CH2:31][CH2:30][O:29][P:28]([CH2:35][C:36]1[CH:41]=[CH:40][C:39]([NH:42][C:2]2[N:7]=[C:6]([NH:8][C:9]3[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=3[C:11](=[O:12])[NH:13][CH3:14])[C:5]([C:19]([F:22])([F:21])[F:20])=[CH:4][N:3]=2)=[C:38]([O:43][CH3:44])[CH:37]=1)(=[O:34])[O:27][CH2:26][CH2:25][O:24][CH3:23]

Participants

3

Reactant 2

HCID 866338612-((2-Chloro-5-(trifluoromethyl)pyrimidin-4-yl)amino)-N-methylbenzamide2×HCID 86654042Bis(2-methoxyethyl)(4-amino-3-methoxybenzyl)phosphonate2×

Product 1

HCID 58292963Bis(2-methoxyethyl) (3-methoxy-4-{[4-{[2-(methylcarbamoyl)phenyl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonateYield 61.7%

Procedure

The title compound was prepared according to Example 102 using 2-{[2-chloro-5-(trifluoromethyl)pyrimidin-4-yl]amino}-N-methylbenzamide (Compound 104A, 50.0 mg, 0.15 mmol) and bis(2-methoxyethyl)(4-amino-3-methoxybenzyl)phosphonate (Compound 217C, 55.4 mg, 0.17 mmol). 58.1 mg (61%) of the desired product obtained after purification. 1H NMR (400 MHz, MeOD) δ ppm 8.24-8.35 (m, 2H), 7.95 (d, J=8.08 Hz, 1H), 7.62 (dd, J=7.83, 1.52 Hz, 1H), 7.46 (ddd, J=8.53, 7.39, 1.52 Hz, 1H), 7.16 (td, J=7.58, 1.01 Hz, 1H), 6.96 (t, J=2.02 Hz, 1H), 6.72-6.80 (m, 1H), 4.05-4.16 (m, 4H), 3.87 (s, 3H), 3.50-3.57 (m, 4H), 3.33 (s, 6H), 3.20-3.29 (m, 2H), 2.89 (s, 3H). MS (ES+): m/z 628.16/629.20 (100/98) [MH+]. HPLC: tR=1.39 min (Micromass TOF: polar—3 min).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-c3add16c106e469c8900aab03d9ebf35
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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