3-Aminophenol → N4-[3-[[4-(ethoxycarbonyl)piperidino]carbonyl]phenyl]-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine

HRID 1783150Notes

Reaction equation

HRID 1783150 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([N:17]3[CH2:22][CH2:21][CH:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:19][CH2:18]3)=[O:16])[CH:10]=2)[C:5]([F:28])=[CH:4][N:3]=1.[OH:29][C:30]1[CH:31]=[C:32]([CH:34]=[CH:35][CH:36]=1)[NH2:33]>>[CH2:26]([O:25][C:23]([CH:20]1[CH2:21][CH2:22][N:17]([C:15]([C:11]2[CH:10]=[C:9]([NH:8][C:6]3[C:5]([F:28])=[CH:4][N:3]=[C:2]([NH:33][C:32]4[CH:34]=[CH:35][CH:36]=[C:30]([OH:29])[CH:31]=4)[N:7]=3)[CH:14]=[CH:13][CH:12]=2)=[O:16])[CH2:18][CH2:19]1)=[O:24])[CH3:27]

Participants

3

Reactant 2

HCID 115683-AminophenolHCID 220610082-chloro-N4-[3-[[4-(ethoxycarbonyl)piperidino]carbonyl]phenyl]-5-fluoro-4-pyrimidineamine

Product 1

HCID 22060267N4-[3-[[4-(ethoxycarbonyl)piperidino]carbonyl]phenyl]-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine

Procedure

In like manner to the preparation of 5-fluoro-N4-(3-hydroxyphenyl)-N2-[4-(3-phenyl-1,2,4-oxadiazol-5-yl)methyleneoxyphenyl]-2,4-pyrimidinediamine, 2-chloro-N4-[3-[[4-(ethoxycarbonyl)piperidino]carbonyl]phenyl]-5-fluoro-4-pyrimidineamine and 3-hydroxyaniline were reacted to provide N4-[3-[[4-(ethoxycarbonyl)piperidino]carbonyl]phenyl]-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine. 1H NMR (CD3OD): δ 7.93 (d, 1H, J=3.6 Hz), 7.89 (t, 1H, J=1.8 Hz), 7.83 (td, 1H, J=1.2 and 8.4 Hz), 7.41 (t, 1H, J=7.8 Hz), 7.11-6.95 (m, 4H), 6.41 (td, 1H, J=1.8 and 7.2 Hz), 4.44 (bd, 1H, J=12.9 Hz), 4.10 (q, 2H, J=7.2 Hz), 3.73 (bd, 1H, J=12.3 Hz), 3.18-2.98 (m, 2H), 2.67-2.55 (m, 1H), 2.05-1.53 (m, 4H), 1.23 (t, 3H, J=7.2 Hz); 19F NMR (282 MHz, CD3OD): −47483; LCMS: purity: 99%; MS (m/e): 480(MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-ea3c599fac3e449ab951cac450b1ac63
Source dataset
uspto-grants-2009_03
Patent number
US07498435B2

Reaction notes

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