Selectfluor → 2-{[3-tert-butyl-4-fluoro-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}-5-methoxybenzoic acid

HRID 915605노트

반응식

HRID 915605 반응식
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:12]=2[C:13]([OH:15])=[O:14])[N:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:28])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[F:29][B-](F)(F)F.F[B-](F)(F)F.ClC[N+]12CC[N+](F)(CC1)CC2>CC#N>[C:1]([C:5]1[C:9]([F:29])=[C:8]([NH:10][C:11]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:12]=2[C:13]([OH:15])=[O:14])[N:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:28])[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 2724933Selectfluor2회HCID 100682862-{[3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}-5-methoxybenzoic acid

생성물 1

HCID 589585972-{[3-tert-butyl-4-fluoro-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}-5-methoxybenzoic acid수율 8%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 2-{[3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}-5-methoxybenzoic acid (Example 4), (49 mg, 0.13 mmol) in CH3CN (1 mL) was added [(1-(chloromethyl)4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)] (SELECTFLUOR®) (46 mg, 0.13 mmol), and the mixture was stirred at rt for 16 h. The solid was filtered off and the filtrate was subjected to HPLC purification with a gradient elution from 10% to 90% acetonitrile in water to afford 4 mg (8%) of the desired product. 1H NMR (300 MHz, CD2Cl2) δ 8.62 (s, 1H), 7.40 (d, 1H), 7.16-7.35 (m, 4H), 7.05 (dd, 1H), 7.76 (dd, 1H), 3.75 (s, 3H), 2.12 (s, 3H), 1.40 (s, 9H). ES-MS m/z 398.2 (MH+); HPLC RT (min) 4.06.

후처리

  1. filtrationThe solid was filtered off
  2. customthe filtrate was subjected to HPLC purification with a gradient elution from 10% to 90% acetonitrile in water

출처 및 근거

ORD 기록
ord-c719dceadcf4410a86e6f2de6c8754b0
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07265144B2

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