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

HRID 1947828Notes

Reaction equation

HRID 1947828 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.[CH2:23]([O:25][P:26]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([NH2:38])=[C:34]([O:39][CH3:40])[CH:33]=1)(=[O:30])[O:27][CH2:28][CH3:29])[CH3:24]>>[CH2:28]([O:27][P:26]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([NH:38][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:34]([O:39][CH3:40])[CH:33]=1)(=[O:30])[O:25][CH2:23][CH3:24])[CH3:29]

Participants

3

Reactant 2

HCID 866338612-((2-Chloro-5-(trifluoromethyl)pyrimidin-4-yl)amino)-N-methylbenzamideHCID 86653997Diethyl(4-amino-3-methoxybenzyl)phosphonate

Product 1

HCID 49821766Diethyl(3-methoxy-4-{[4-{[2-(methylcarbamoyl)phenyl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate

Procedure

Prepared according to the procedure described for Example 48 using (2-{[2-chloro-5-(trifluoromethyl)pyrimidin-4-yl]amino}-N-methylbenzamide and diethyl(4-amino-3-methoxybenzyl)phosphonate. 1H NMR (CD3OD, 400 MHz): δ=1.27 (t, J=7.07 Hz, 6H), 2.90 (s, 3H), 3.20-3.28 (m, 2H), 3.91 (s, 3H), 4.01-4.11 (m, 4H), 6.80 (dt, J=8.21, 2.21 Hz, 1H), 6.99 (t, J=2.15 Hz, 1H), 7.19 (td, J=7.58, 1.26 Hz, 1H), 7.48 (ddd, J=8.46, 7.20, 1.52 Hz, 1H), 7.64 (dd, J=7.83, 1.52 Hz, 1H), 7.96 (d, J=8.08 Hz, 1H), 8.30-8.36 (m, 2H). MS (ES+): m/z 568.1542 [MH+] (TOF, polar).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-683b48efa6094c3ba6f0126303d9f0d4
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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