Trifluoroacetic acid → 5-{2-[3-(1-Hydroxyethyl)-phenylamino]-pyrimidin-4-yl}-thiophene-2-sulfonic acid dimethylamide

HRID 1012170

반응식

HRID 1012170 반응식
[CH3:1][N:2]([CH3:21])[S:3]([C:6]1[S:7][C:8]([C:11]2[CH:16]=[CH:15][N:14]=[C:13](S(C)(=O)=O)[N:12]=2)=[CH:9][CH:10]=1)(=[O:5])=[O:4].[NH2:22][C:23]1[CH:24]=[C:25]([CH:29]([OH:31])[CH3:30])[CH:26]=[CH:27][CH:28]=1.FC(F)(F)C(O)=O>CS(C)=O>[CH3:1][N:2]([CH3:21])[S:3]([C:6]1[S:7][C:8]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([CH:29]([OH:31])[CH3:30])[CH:24]=3)[N:12]=2)=[CH:9][CH:10]=1)(=[O:5])=[O:4]

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 2224611-(3-Aminophenyl)ethanolHCID 594686055-(2-Methanesulfonyl-pyrimidin-4-yl)-thiophene-2-sulfonic acid dimethylamide

생성물 1

HCID 166666025-{2-[3-(1-Hydroxyethyl)-phenylamino]-pyrimidin-4-yl}-thiophene-2-sulfonic acid dimethylamide수율 62.6%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

반응 조건

온도
100 °C

실험 절차

5-(2-Methanesulfonyl-pyrimidin-4-yl)-thiophene-2-sulfonic acid dimethylamide (19.8 mg, 0.057 mmol), 1-(3-aminophenyl)ethanol (11.7 mg, 0.085 mmol) and trifluoroacetic acid (6.5 uL, 0.085 mmol) were combined in DMSO (0.5 M) and the mixture was heated in a capped vial at 100° C. for 16 hours. The dark solution was diluted with DMSO and purified by preparative LC. 5-{2-[3-(1-Hydroxyethyl)-phenylamino]-pyrimidin-4-yl}-thiophene-2-sulfonic acid dimethylamide (14.4 mg, 62.6%) was obtained as a brown solid after lyophilization. 1H NMR (500 MHz, DMSO-d6) δ 1.35 (d, J=6 Hz, 3H), 2.70 (s, 6H), 4.70 (m, 1H), 5.12 (d, J=4 Hz, 1H), 6.97 (br d, J=7 Hz, 1H), 7.24 (t, J=7.5 Hz, 1H), 7.46 (d, J=5.5 Hz, 1H), 7.49 (br d, J=6.5 Hz, 1H), 7.71 (d, J=4 Hz, 1H), 7.91 (br s, 1H), 8.12 (d, J=4 Hz, 1H), 8.58 (d, J=5.0 Hz, 1H), 9.75 (s, 1H). MS: m/z 405 (M+H+).

후처리

  1. custompurified by preparative LC

출처 및 근거

ORD 기록
ord-f354dbe24c414abdb67940f570fdaf2b
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977481B2

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