3-[4-(2-Chloro-6-fluorobenzyl)piperazino]propylamine → HCID 22060773, compound

HRID 1829356Notes

Reaction equation

HRID 1829356 reaction equation
[CH2:1]1[CH2:10][O:9][C:8]2[CH:7]=[CH:6][C:5]([NH:11][C:12]3[C:17]([F:18])=[CH:16][N:15]=[C:14]([NH:19][C:20]4[CH:25]=[CH:24]C=C(O)C=4)[N:13]=3)=[CH:4][C:3]=2[O:2]1.ClC1N=C(NC2C=CC3OCCOC=3C=2)C(F)=CN=1.[Cl:46][C:47]1[CH:63]=[CH:62][CH:61]=[C:60]([F:64])[C:48]=1[CH2:49][N:50]1[CH2:55][CH2:54][N:53](CCCN)[CH2:52][CH2:51]1>>[Cl:46][C:47]1[CH:63]=[CH:62][CH:61]=[C:60]([F:64])[C:48]=1[CH2:49][N:50]1[CH2:51][CH2:52][N:53]([CH2:24][CH2:25][CH2:20][NH:19][C:14]2[N:13]=[C:12]([NH:11][C:5]3[CH:6]=[CH:7][C:8]4[O:9][CH2:10][CH2:1][O:2][C:3]=4[CH:4]=3)[C:17]([F:18])=[CH:16][N:15]=2)[CH2:54][CH2:55]1

Participants

4

Reactant 3

HCID 27794453-[4-(2-Chloro-6-fluorobenzyl)piperazino]propylamineHCID 22060334N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-primidinediamineHCID 220603622-chloro-5-fluoro-N-(3,4-ethylenedioxyphenyl)-4-pyrimidineamine

Product 1

HCID 22060773HCID 22060773, compound

Procedure

In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and 3-[4-(2-chloro-6-fluorobenzyl)piperazino]propylamine were reacted to yield N2-[3-[4-(2-chloro-6-fluorobenzyl)piperazino]propyl]-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 7.79 (d, 1H, J=3.0 Hz), 7.37 (d, 1H, J=2.4 Hz), 7.19–7.15 (m, 2H), 7.00–6.93 (m, 2H), 6.81 (d, 1H, J=8.7 Hz), 6.56 (d, 1H, J=2.7 Hz), 5.48 (bs, 1H), 4.27–4.21 (m, 4H), 3.70 (d, 2H, J=1.8 Hz), 3.36 (q, 2H, J=6.3 Hz), 2.68–2.35 (m, 10H), 1.75 (q, 2H, J=6.3 Hz); 19F NMR (CDCl3): −31693, −48483; LCMS: ret. time: 18.20 min.; purity: 97%; MS (m/e): 532 (MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-a8d3487509f945e38e0df32e836ede71
Source dataset
uspto-grants-2006_06
Patent number
US07060827B2

Reaction notes

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