2-(3-Ethoxyphenoxy)-N-[4-hydroxy-2-(isobutylamino)phenyl]acetamide → 2-[(3-Ethoxyphenoxy)methyl]-1-isobutylbenzimidazol-6-ol

HRID 537314노트

반응식

HRID 537314 반응식
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:24]=[CH:25][CH:26]=1)[O:7][CH2:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:13]=1[NH:19][CH2:20][CH:21]([CH3:23])[CH3:22])=O)[CH3:2]>CC(O)=O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:24]=[CH:25][CH:26]=1)[O:7][CH2:8][C:9]1[N:19]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:13]2[CH:14]=[C:15]([OH:18])[CH:16]=[CH:17][C:12]=2[N:11]=1)[CH3:2]

참가 물질

3

반응물 1

HCID 866892922-(3-Ethoxyphenoxy)-N-[4-hydroxy-2-(isobutylamino)phenyl]acetamide

생성물 1

HCID 866892932-[(3-Ethoxyphenoxy)methyl]-1-isobutylbenzimidazol-6-ol수율 87.4%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A 250 mL flask fitted with a stir-bar and condenser was charged with amine 65b (10.0 g, 27.9 mmol) and AcOH (100 mL). The resultant solution was heated in a 100° C. bath for 1 hr, then concentrated in vacuo to a brown oil. The oil was taken up in EtOAc (200 mL) and washed with saturated NaHCO3 (2×100 mL) and brine (100 mL). Isopropanol (50 mL) and CH2Cl2 (50 mL) were added to break the emulsion. The organic solution was filtered through phase separation paper and concentrated in vacuo to a red-tan solid. The solid was triturated with hexanes:EtOAc 9:1 (50 mL), filtered, pressed with rubber dam, and rinsed with hexanes:EtOAc 9:1 (2×20 mL). The solid was dried to give 8.3 g of 66b as a tan solid (87%). 1H NMR (300 MHz, CDCl3): δ 8.84 (s, 1H), 7.37 (d, 1H), 7.02 (t, 1H), 6.70 (dd, 1H), 6.65 (d, 1H), 6.48 (dd, 1H), 6.44 (t, 1H), 6.37 (dd, 1H), 5.10 (s, 2H), 3.86 (t, 2H), 3.81 (d, 2H), 2.15 (nonet, 1H), 1.23 (t, 3H), 0.78 (d, 6H) ppm. HPLC analysis (0:10:90 H2O:A1:MeOH) showed a purity of 99% with a retention time of 3.5 min.

후처리

  1. customA 250 mL flask fitted with a stir-bar and condenser
  2. concentrationconcentrated in vacuo to a brown oil
  3. washwashed with saturated NaHCO3 (2×100 mL) and brine (100 mL)
  4. additionIsopropanol (50 mL) and CH2Cl2 (50 mL) were added
  5. filtrationThe organic solution was filtered through phase separation paper
  6. concentrationconcentrated in vacuo to a red-tan solid
  7. customThe solid was triturated with hexanes:EtOAc 9:1 (50 mL)
  8. filtrationfiltered
  9. washrinsed with hexanes:EtOAc 9:1 (2×20 mL)
  10. customThe solid was dried

출처 및 근거

ORD 기록
ord-2692b1236ffc4e5d83f908e0d8042ce6
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859780B2

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