1,4-Benzodioxan-6-ylamine → HCID 22060655, compound
Reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[C:16]([F:17])=[CH:15][N:14]=[C:13]([NH:18][C:19]3[CH:24]=[CH:23][C:22]4[O:25][CH2:26][CH2:27][O:28][C:21]=4[CH:20]=3)N=2)=[CH:6][CH:5]=1)[CH3:2].ClC1N=C(N[C:37]2[CH:42]=CC(OCCCCCC)=[CH:39][CH:38]=2)C(F)=CN=1.[CH2:51]1COC2C=CC(N)=CC=2O1>>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[C:16]([F:17])=[CH:15][N:14]=[C:13]([NH:18][C:19]3[CH:24]=[CH:23][C:22]4[O:25][CH2:26][CH2:27][O:28][C:21]=4[CH:20]=3)[CH:51]=2)=[CH:6][CH:5]=1)[CH2:2][CH2:42][CH2:37][CH2:38][CH3:39]Participants
Procedure
In like manner to the preparartion of N4-(4-ethyloxyphenyl)-N2-(3,4-ethylenedioxyphenyl)-5-fluoro-2,4-pyrimidinediamine, the reaction of 2-chloro-N4-(4-n-hexyloxyphenyl)-5-fluoro-4-pyrimidineamine with 3,4-ethylenedioxyaniline gave N4-(4-n-hexyloxyphenyl)-N2-(3,4-ethylenedioxyphenyl)-5-fluoro-2,4-pyridinediamine. The crude product was purified by chromatography (2:1 CHCl3/EtOAc) (0.22 g, 69%) as a tan solid: Rf 0.54 (4:1 CHCl3/EtOAc); mp 124.0–125.2° C. (DSC); 1H NMR (300 MHz, CDCl3) δ 7.88 (d, J=3.2 Hz, 1H), 7.47 (d, J=8.9 Hz, 2H), 7.18 (d, J=2.4 Hz, 1H), 6.91–6.86 (m, 3H), 6.78–6.74 (m, 2H), 6.62 (d, J=1.8 Hz, 1H), 4.26–4.22 (m, 4H), 3.96 (t, J=6.5, 2H), 1.83–1.74 (m, 2H), 1.51–1.42 (m, 2H), 1.36–1.32 (m, 4H), 0.93–0.89 (t, J=6.7 Hz, 3H), 13C NMR (75 MHz, CDCl3) δ 156.1, 150.5, 143.5, 143.0, 142.8, 140.2, 139.9, 139.5, 139.2, 133.9, 130.7, 123.1, 117.1, 115.0, 113.5, 109.3, 68.5, 64.7, 64.5, 31.8, 29.5, 25.9, 22.8, 14.2; IR (ATR) 3378 cm−1; ESI MS m/z 439 [C24H27FN4O3+H]+; HPLC (Method A)>99% (AUC), tR=14.6 min. Anal. Calcd for C24H27FN4O3: C, 65.74; H, 6.21; N, 12.78. Found: C, 65.52; H, 6.23; N, 12.66.
Sources & evidence
- ORD record
- ord-5e9dcf726191491d9dcaf8f9c94a9446
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07557210B2
Reaction notes
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