Cesium carbonate → 4-(2-Fluoro-4-(3-(2-phenylacetyl)thioureido)phenoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl pivalate

HRID 2114021노트

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HRID 2114021 반응식
[C:1]([O:7][C:8]1[C:9]([CH3:18])=[C:10]2[N:15]([CH:16]=1)[N:14]=[CH:13][N:12]=[C:11]2Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[F:19][C:20]1[CH:21]=[C:22]([NH:27][C:28]([NH:30][C:31](=[O:39])[CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[S:29])[CH:23]=[CH:24][C:25]=1[OH:26].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:1]([O:7][C:8]1[C:9]([CH3:18])=[C:10]2[N:15]([CH:16]=1)[N:14]=[CH:13][N:12]=[C:11]2[O:26][C:25]1[CH:24]=[CH:23][C:22]([NH:27][C:28]([NH:30][C:31](=[O:39])[CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[S:29])=[CH:21][C:20]=1[F:19])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 210814961-(3-Fluoro-4-hydroxyphenyl)-3-(2-phenylacetyl)thioureaHCID 210816794-Chloro-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl 2,2-dimethylpropanoate2회

생성물 1

HCID 116134924-(2-Fluoro-4-(3-(2-phenylacetyl)thioureido)phenoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl pivalate수율 25%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

A vial was charged with 4-chloro-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl pivalate (13.3 mg, 0.19 mmol, Compound D of Example 1), 1-(3-fluoro-4-hydroxyphenyl)-3-(2-phenylacetyl)thiourea (16 mg, 0.05 mmol), cesium carbonate (spatula tip) and DMF (2 mL) and warmed to 100° C. for 26 h. The mixture was concentrated in vacuo. The residue was purified by flash chromatography to give the title compound (6.2 mg, 25%) as a white solid. 1H NMR (CDCl3) 12.46 (s, 1H), 8.50 (s, 1H), 7.88 (m, 3H), 7.40 (m, 4H), 7.31 (m, 2H), 3.75 (s, 3H), 2.44 (s, 3H), 1.40 (s, 9H); MS(ESI+) m/z 536 (M+H)+.

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-ea6bdcd9ec984f94948c2df91a33ec64
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07432373B2

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