Sodium hydride → 1-(5-t-butyl-2-{3-[5-(4-methoxy-benzyl)-1,1,4-trioxo-1lambda6-[1,2,5]thiadiazolidin-2-ylmethyl]-phenyl}-2H-pyrazol-3-yl)-3-(4-fluoro-phenyl)-urea

HRID 1270533노트

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HRID 1270533 반응식
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][N:8]2[C:12](=[O:13])[CH2:11][NH:10][S:9]2(=[O:15])=[O:14])=[CH:5][CH:4]=1.[H-].[Na+].[C:20]([C:24]1[CH:25]=[C:26]([NH:37][C:38]([NH:40][C:41]2[CH:46]=[CH:45][C:44]([F:47])=[CH:43][CH:42]=2)=[O:39])[N:27]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([CH2:35]Cl)[CH:30]=2)[N:28]=1)([CH3:23])([CH3:22])[CH3:21]>CN(C=O)C>[C:20]([C:24]1[CH:25]=[C:26]([NH:37][C:38]([NH:40][C:41]2[CH:46]=[CH:45][C:44]([F:47])=[CH:43][CH:42]=2)=[O:39])[N:27]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([CH2:35][N:10]3[CH2:11][C:12](=[O:13])[N:8]([CH2:7][C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:17][CH:16]=4)[S:9]3(=[O:15])=[O:14])[CH:30]=2)[N:28]=1)([CH3:23])([CH3:21])[CH3:22]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 184498681-[5-t-butyl-2-(3-chloromethyl-phenyl)-2H-pyrazol-3-yl]-3-(4-fluoro-phenyl)-ureaHCID 588428642-(4-Methoxybenzyl)-1,2,5-thiadiazolidin-3-one 1,1-dioxide

생성물 1

HCID 685845351-(5-t-butyl-2-{3-[5-(4-methoxy-benzyl)-1,1,4-trioxo-1lambda6-[1,2,5]thiadiazolidin-2-ylmethyl]-phenyl}-2H-pyrazol-3-yl)-3-(4-fluoro-phenyl)-urea

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
0 °C

실험 절차

To a solution of 2-(4-methoxy-benzyl)-1,1-dioxo-1λ6-[1,2,5]thiadiazolidin-3-one (64 mg, 0.25 mmol) in anhydrous DMF (2 mL) was added NaH (11 mg, 0.27 mmol) at 0° C. After stirred for 0.5 h at 0° C., a solution of 1-[5-t-butyl-2-(3-chloromethyl-phenyl)-2H-pyrazol-3-yl]-3-(4-fluoro-phenyl)-urea from the previous reaxtion (100 mg, 0.25 mmol) in anhydrous DMF (2 mL) was added to the reaction mixture, then was stirred overnight at RT. The crude was purified through prepared-HPLC to yield 1-(5-t-butyl-2-{3-[5-(4-methoxy-benzyl)-1,1,4-trioxo-1λ6-[1,2,5]thiadiazolidin-2-ylmethyl]-phenyl}-2H-pyrazol-3-yl)-3-(4-fluoro-phenyl)-urea (45 mg). 1H NMR (DMSO-d6): 8.95 (s, 1H), 8.37 (s, 1H), 7.50–7.54 (m, 3H), 7.36–7.41 (m, 3H), 7.25 (d, J=8.8 Hz, 2H), 7.07 (t, J=8.8 Hz, 2H), 6.87 (d, J=8.4 Hz, 2H), 6.35 (s, 1H), 4.64 (s, 2H), 4.47 (s, 2H), 4.19 (s, 2H), 3.75 (s, 3H), 1.26 (s, 9H). MS (ESI) m/z: 515 (M+H+).

후처리

  1. stirringwas stirred overnight at RT
  2. customThe crude was purified through prepared-HPLC

출처 및 근거

ORD 기록
ord-d2740019dcde4d088d4fb69fcdafbc0e
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07202257B2

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