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

HRID 511305Notes

Reaction equation

HRID 511305 reaction equation
[F:1][C:2]([F:24])([F:23])[CH2:3][O:4][P:5]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([O:21][CH3:22])[CH:15]=1)(=[O:12])[O:6][CH2:7][C:8]([F:11])([F:10])[F:9].Cl[C:26]1[N:31]=[C:30]([NH:32][C:33]2[CH:42]=[CH:41][CH:40]=[CH:39][C:34]=2[C:35]([NH:37][CH3:38])=[O:36])[C:29]([C:43]([F:46])([F:45])[F:44])=[CH:28][N:27]=1>>[F:24][C:2]([F:1])([F:23])[CH2:3][O:4][P:5]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:26]2[N:31]=[C:30]([NH:32][C:33]3[CH:42]=[CH:41][CH:40]=[CH:39][C:34]=3[C:35](=[O:36])[NH:37][CH3:38])[C:29]([C:43]([F:46])([F:44])[F:45])=[CH:28][N:27]=2)=[C:16]([O:21][CH3:22])[CH:15]=1)(=[O:12])[O:6][CH2:7][C:8]([F:9])([F:10])[F:11]

Participants

3

Reactant 2

HCID 866338612-((2-Chloro-5-(trifluoromethyl)pyrimidin-4-yl)amino)-N-methylbenzamideHCID 86654014Bis(2,2,2-trifluoroethyl)(4-amino-3-methoxybenzyl)phosphonate2×

Product 1

HCID 58293030Bis(2,2,2-trifluoroethyl)(3-methoxy-4-{[4-{[2-(methylcarbamoyl)phenyl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate

Procedure

The title compound was prepared according to the procedure for Example 102 bis(2,2,2-trifluoroethyl)(4-amino-3-methoxybenzyl)phosphonate (Compound 114A, 38 mg, 0.1 mmol) and 2-(2-chloro-5-(trifluoromethyl)pyrimidin-4-ylamino)-N-methylbenzamide (33 mg, 0.1 mmol). The reaction mixture was concentrated in vacuo and the residue was purified by HPLC to afford the title compound. 1H-NMR (DMSO-d6, 400 MHz): δ=2.73 (s, 3 H), 3.52 (d, J=21.6 Hz, 2 H), 3.73 (s, 3 H), 4.60-4.65 (m, 4 H), 6.81 (d, J=7.6 Hz, 1 H), 6.98 (s, 1 H), 7.05 (t, J=7.6 Hz, 1 H), 7.34 (t, J=7.2 Hz, 1 H), 7.57 (d, J=8.0 Hz, 1 H), 7.65 (dd, J=1.2, 7.6 Hz, 1 H), 8.34 (s, 1 H), 8.38 (s, 1 H), 8.68 (d, J=4.4 Hz, 1 H), 8.71 (s, 1 H), 11.42 (s, 1 H). MS (ES+): m/z 676.05 [MH+]; HPLC: tR=3.69 min (ZQ3, polar—5 min).

Workup

  1. customThe title compound was prepared
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-3193ba6dfa00473bb10cb46c3683f668
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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