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

HRID 1947873Notes

Reaction equation

HRID 1947873 reaction equation
[OH:1][CH2:2][CH2:3][O:4][P:5]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([O:19][CH3:20])[CH:13]=1)(=[O:10])[O:6][CH2:7][CH2:8][OH:9].Cl[C:22]1[N:27]=[C:26]([NH:28][C:29]2[CH:38]=[CH:37][CH:36]=[CH:35][C:30]=2[C:31]([NH:33][CH3:34])=[O:32])[C:25]([C:39]([F:42])([F:41])[F:40])=[CH:24][N:23]=1>>[OH:9][CH2:8][CH2:7][O:6][P:5]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:22]2[N:27]=[C:26]([NH:28][C:29]3[CH:38]=[CH:37][CH:36]=[CH:35][C:30]=3[C:31](=[O:32])[NH:33][CH3:34])[C:25]([C:39]([F:42])([F:40])[F:41])=[CH:24][N:23]=2)=[C:14]([O:19][CH3:20])[CH:13]=1)(=[O:10])[O:4][CH2:3][CH2:2][OH:1]

Participants

3

Reactant 2

HCID 866338612-((2-Chloro-5-(trifluoromethyl)pyrimidin-4-yl)amino)-N-methylbenzamide2×HCID 86654012Bis(2-hydroxyethyl)(4-amino-3-methoxybenzyl)phosphonate2×

Product 1

HCID 49821271Bis(2-hydroxyethyl)(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 using bis(2-hydroxyethyl)(4-amino-3-methoxybenzyl)phosphonate (Compound 113A, 30 mg, 0.1 mmol) and 2-(2-chloro-5-(trifluoromethyl)pyrimidin-4-ylamino)-N-methylbenzamide (Compound 104A, 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=2.83 (s, 3H), 3.35 (d, J=21.6 Hz, 2H), 3.60 (dd, J=5.2, 10.4 Hz, 4H), 3.84 (s, 3H), 3.99-4.03 (m, 4H), 4.95 (t, J=5.2 Hz, 2H), 6.92 (d, J=7.6 Hz, 1H), 7.11 (s, 1H), 7.16 (t, J=7.6 Hz, 1H), 7.45 (m, 1H), 7.61 (d, J=8.0 Hz, 1H), 7.73 (dd, J=1.2, 8.0 Hz, 1H), 8.43 (s, 1H), 8.48 (m, 1H), 8.80 (m, 2H), 11.49 (s, 1H). MS (ES+): m/z 600.11 [MH+]; HPLC: tR=2.80 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-d8c2c76a7e054a8a91648a4b8cc1c0d6
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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