Potassium Carbonate → HCID 71263626, 화합물

HRID 1424848노트

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HRID 1424848 반응식
[CH:1]1([C:4]2[C:5]([N:24]([C:29]3[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=3)[S:25]([CH3:28])(=[O:27])=[O:26])=[CH:6][C:7]3[O:11][C:10]([C:12]4[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=4)=[C:9]([C:19]([NH:21][CH3:22])=[O:20])[C:8]=3[CH:23]=2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:43][B:44]1[O:48]C(C)(C)C(C)(C)[O:45]1>CC#N>[CH:1]1([C:4]2[C:5]([N:24]([C:29]3[CH:30]=[CH:31][C:32]([O:35][CH2:43][B:44]([OH:48])[OH:45])=[CH:33][CH:34]=3)[S:25]([CH3:28])(=[O:27])=[O:26])=[CH:6][C:7]3[O:11][C:10]([C:12]4[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=4)=[C:9]([C:19](=[O:20])[NH:21][CH3:22])[C:8]=3[CH:23]=2)[CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 109551102-(Bromomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 131732298HCID 131732298, 화합물

생성물 1

HCID 71263626HCID 71263626, 화합물수율 81%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
65 °C

실험 절차

A mixture of 5-cyclopropyl-2-(4-fluorophenyl)-6-(N-(4-hydroxyphenyl)methylsulfonamido)-N-methylbenzofuran-3-carboxamide (85.0 mg, 0.172 mmol), potassium carbonate (0.119 g, 0.859 mmol), and 2-(bromomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.152 g, 0.688 mmol) in MeCN (3 mL) in a sealed tube was heated to 65° C. with stirring. After 2 hours the mixture was cooled to RT, filtered to remove solids, and the filtrate concentrated to dryness at reduced pressure. The residue was subjected to RP-HPLC purification (C18, MeCN/water/0.1% formic acid) followed by lyophilization from MeCN/water to give the title compound (77 mg, 81%) as a white powder. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.40-8.47 (m, 1H) 8.15 (s, 1H) 8.03 (s, 2H) 7.97 (dd, J=8.8, 5.4 Hz, 2H) 7.53 (d, J=9.0 Hz, 2H) 7.40 (t, J=8.9 Hz, 2H) 7.12 (s, 1H) 6.90 (d, J=9.1 Hz, 2H) 3.58 (s, 2H) 3.33 (s, 3H) 2.82 (d, J=4.5 Hz, 3H) 2.24-2.38 (m, 1H) 0.76-1.10 (m, 3H) 0.47 (br. s., 1H). LCMS (m/z, ES+)=553 (M+H+).

후처리

  1. temperatureAfter 2 hours the mixture was cooled to RT
  2. filtrationfiltered
  3. customto remove solids
  4. concentrationthe filtrate concentrated to dryness at reduced pressure
  5. customThe residue was subjected to RP-HPLC purification (C18, MeCN/water/0.1% formic acid)

출처 및 근거

ORD 기록
ord-b60211fcfa7d465593ff1dc832dd384b
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927593B2

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