Lithium Hydroxide → N2-(2-carboxyindol-5-yl)-5-fluoro-N4-(3-hydroxyphenyl)-2,4-pyrimidinediamine

HRID 734021

반응식

HRID 734021 반응식
N1C=CC(N)=CC=1N.C([O:11][C:12]([C:14]1[NH:15][C:16]2[C:21]([CH:22]=1)=[CH:20][C:19]([NH:23][C:24]1[N:29]=[C:28]([NH:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([OH:37])[CH:32]=3)[C:27]([F:38])=[CH:26][N:25]=1)=[CH:18][CH:17]=2)=[O:13])C.[Li+].[OH-]>>[C:12]([C:14]1[NH:15][C:16]2[C:21]([CH:22]=1)=[CH:20][C:19]([NH:23][C:24]1[N:29]=[C:28]([NH:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([OH:37])[CH:32]=3)[C:27]([F:38])=[CH:26][N:25]=1)=[CH:18][CH:17]=2)([OH:13])=[O:11]

참가 물질

4

반응물 3

HCID 3939Lithium HydroxideHCID 680362,4-DiaminopyridineHCID 22060970N2-(2-ethoxycarbonylindol-5-yl)-5-fluoro-N4-(3-hydroxyphenyl)-2,4-pyrimidinediamine

생성물 1

HCID 22060545N2-(2-carboxyindol-5-yl)-5-fluoro-N4-(3-hydroxyphenyl)-2,4-pyrimidinediamine

실험 절차

In a manner similar to the preparation of N4-(4-tert-butylphenyl)-5-fluoro-N2-[2,3-dihydro-2-carboxy)benzofuran-5-yl]-2,4-pyridinediamine, N2-(2-ethoxycarbonylindol-5-yl)-5-fluoro-N4-(3-hydroxyphenyl)-2,4-pyrimidinediamine upon LiOH treatment gave N2-(2-carboxyindol-5-yl)-5-fluoro-N4-(3-hydroxyphenyl)-2,4-pyrimidinediamine. 1H NMR (CD3OD): δ 7.83 (m, 1H), 7.73 (s, 1H), 7.50 (bd, 1H, J=8.7 Hz), 7.30–7.11 (m, 5H), 6.68 (bd, 1H); LCMS: ret. time: 16.50 min.; purity: 97%; MS (m/e): 380 (MH+).

출처 및 근거

ORD 기록
ord-cb314603cf8b44f0b62d99beae2dd134
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07589200B2

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