1,4-Benzodioxan-6-ylamine → HCID 22060833, compound

HRID 1932072Notes

Reaction equation

HRID 1932072 reaction equation
[CH2:1]1[CH2:10][O:9][C:8]2[CH:7]=[CH:6][C:5]([NH:11]C3C(F)=CN=C(NC4C=CC=C(O)C=4)N=3)=[CH:4][C:3]=2[O:2]1.Cl[C:28]1[N:33]=[C:32]([NH:34][CH2:35][C:36]2[C:40]3[CH:41]=[C:42]([Cl:45])[CH:43]=[CH:44][C:39]=3[S:38][CH:37]=2)[C:31]([F:46])=[CH:30][N:29]=1.C1COC2C=CC(N)=CC=2O1>>[Cl:45][C:42]1[CH:43]=[CH:44][C:39]2[S:38][CH:37]=[C:36]([CH2:35][NH:34][C:32]3[C:31]([F:46])=[CH:30][N:29]=[C:28]([NH:11][C:5]4[CH:6]=[CH:7][C:8]5[O:9][CH2:10][CH2:1][O:2][C:3]=5[CH:4]=4)[N:33]=3)[C:40]=2[CH:41]=1

Participants

4

Reactant 3

HCID 891481,4-Benzodioxan-6-ylamineHCID 22060334N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-primidinediamineHCID 22060342HCID 22060342, compound

Product 1

HCID 22060833HCID 22060833, 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-[(5-chloro-1-benzothiophen-3-yl)methyl]-5-fluoro-4-pyrimidineamine and 3,4-ethylenedioxyaniline were reacted to yield N4-[(5-chloro-1-benzothiophen-3-yl)methyl]-N2-(3,4-ethylenedioxyphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 8.08 (d, 1H, J=1.8 Hz), 8.02 (d, 1H, J=8.7 Hz), 7.97 (d, 1H, J=4.8 Hz), 7.63 (s, 1H), 7.42 (dd, 1H, J=1.8 and 9.3 Hz), 7.07 (bs, 1H), 6.85 (dd, 1H, J=2.4 and 8.7 Hz), 6.56 (d, 1H, J=8.7 Hz), 4.77 (s, 1H), 4.75 (s, 1H), 4.14 (s, 4H); LCMS: ret. time: 25.89 min.; purity: 97%; MS (m/e): 444 (MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-34c5f1f6ffb34be79331297bf45d033a
Source dataset
uspto-grants-2012_05
Patent number
US08188276B2

Reaction notes

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