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2-Chloro-6-fluorobenzyl bromide → 1-[1-(2-Chloro-6-fluorobenzyl)-1H-benzimidazol-4-yl]-5-hydroxy-2-methylpyridin-4(1H)-one

HRID 1056897
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HRID 1056897 반응식
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([N:10]3[CH:15]=[C:14]([OH:16])[C:13](=[O:17])[CH:12]=[C:11]3[CH3:18])[C:4]=2[N:3]=[CH:2]1.[Cl:19][C:20]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:21]=1[CH2:22]Br>CN(C=O)C>[Cl:19][C:20]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:21]=1[CH2:22][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([N:10]3[CH:15]=[C:14]([OH:16])[C:13](=[O:17])[CH:12]=[C:11]3[CH3:18])[C:4]=2[N:3]=[CH:2]1
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참가 물질

4

반응물 2

HCID 27736252-Chloro-6-fluorobenzyl bromide2회HCID 674202641-(1H-Benzimidazol-4-yl)-5-hydroxy-2-methylpyridin-4(1H)-one

생성물 1

HCID 699322271-[1-(2-Chloro-6-fluorobenzyl)-1H-benzimidazol-4-yl]-5-hydroxy-2-methylpyridin-4(1H)-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

1-(1H-Benzimidazol-4-yl)-5-hydroxy-2-methylpyridin-4(1H)-one (30 mg, 0.124 mmol) and 2-chloro-6-fluorobenzyl bromide (20 μï, 0.146 mmol) were combined in DMF (0.5 ml) then heated to 100° C. After 3 h LC/MS indicated the reaction was incomplete. The mixture was cooled to RT and 10 μL of 2-chloro-6-fluorobenzyl bromide was added. The mixture was heated to 100° C. After 1 hr the mixture was cooled to RT and purified directly by preparative reversed-phase HPLC (20×150 mm Waters Sunfire (0.1% TFA), 5-40% ACN/water over 20 min at 20 mL/min). Fractions containing the product were pooled then applied to a Phenomenex Strata-X-C ion exchange column. The column was washed with H20 and MeOH (discard) then with 10% concentrated NH4OH in MeOH (collect). The collected fraction was concentrated to give 1-[1-(2-Chloro-6-fluorobenzyl)-1H-benzimidazol-4-yl]-5-hydroxy-2-methylpyridin-4(1H)-one as an off-white solid. 1H NMR (500 MHz, d6-DMSO) δ 8.43 (s, 1H), 7.66 (d, J=8.3 Hz, 1H), 7.52-7.29 (m, 6H), 6.24 (s, 1H), 5.70 (s, 2H), 1.90 (s, 3H). HRMS (ESI) calc (M+H)+=384.0910. found 384.0913.

후처리

  1. temperatureThe mixture was cooled to RT
  2. temperatureThe mixture was heated to 100° C
  3. temperatureAfter 1 hr the mixture was cooled to RT
  4. custompurified directly by preparative reversed-phase HPLC (20×150 mm Waters Sunfire (0.1% TFA), 5-40% ACN/water over 20 min at 20 mL/min)
  5. additionFractions containing the product
  6. washThe column was washed with H20 and MeOH (discard)
  7. concentrationThe collected fraction was concentrated

출처 및 근거

ORD 기록
ord-cd7fd354eaf243b881648dabe79efea0
출처 데이터셋
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09399651B2

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