6-Aminoindole → 5-fluoro-N4-(3-hydroxyphenyl)-N2-[(1H)-indol-6-yl]-2,4-pyrimidinediamine

HRID 76573

Reaction equation

HRID 76573 reaction equation
C1COC2C=CC(NC3C(F)=CN=C(NC4C=CC=C(O)C=4)N=3)=CC=2O1.Cl[C:28]1[N:33]=[C:32]([NH:34][C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([OH:41])[CH:36]=2)[C:31]([F:42])=[CH:30][N:29]=1.[NH2:43][C:44]1[CH:52]=[C:51]2[C:47]([CH:48]=[CH:49][NH:50]2)=[CH:46][CH:45]=1>>[F:42][C:31]1[C:32]([NH:34][C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([OH:41])[CH:36]=2)=[N:33][C:28]([NH:43][C:44]2[CH:52]=[C:51]3[C:47]([CH:48]=[CH:49][NH:50]3)=[CH:46][CH:45]=2)=[N:29][CH:30]=1

Participants

4

Reactant 3

HCID 2560966-AminoindoleHCID 22060334N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-primidinediamineHCID 220604512-chloro-5-fluoro-N-(3-hydroxyphenyl)-4-pyrimidineamine

Product 1

HCID 220602765-fluoro-N4-(3-hydroxyphenyl)-N2-[(1H)-indol-6-yl]-2,4-pyrimidinediamine

Procedure

In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N4-(3-hydroxyphenyl)-4-pyrimidineamine and 6-aminoindole were reacted to yield 5-fluoro-N4-(3-hydroxyphenyl)-N2-[(1H)-indol-6-yl]-2,4-pyrimidinediamine LCMS: ret. time: 18.13 min.; purity: 96%; MS (m/e): 336 (MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-67f9ed22e087447090cc71f70d94b4f1
Source dataset
uspto-grants-2014_09
Patent number
US08835430B2

Linked notes

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