Triethylamine → N-[5-[(E)-N'-hydroxycarbamimidoyl]-2-pyridinyl]-3,5-bis(phenylmethoxy)benzamide

HRID 552609노트

반응식

HRID 552609 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:23]=[C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:25]=1)[C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][N:16]=1)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl.[NH2:42][OH:43]>C(O)C>[CH2:27]([O:26][C:24]1[CH:23]=[C:11]([CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:25]=1)[C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([NH:42][OH:43])=[NH:22])=[CH:17][N:16]=1)=[O:13])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 230729493,5-bis(benzyloxy)-N-(5-cyanopyridin-2-yl)benzamide

생성물 1

HCID 178513344N-[5-[(E)-N'-hydroxycarbamimidoyl]-2-pyridinyl]-3,5-bis(phenylmethoxy)benzamide

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 3,5-bis(benzyloxy)-N-(5-cyanopyridin-2-yl)benzamide (212 mg, 0.49 mmol), triethylamine (170 μL, 1.22 mmol) and hydroxylamine hydrochloride (85 mg, 1.22 mmol) in ethanol (5 mL) was heated at reflux overnight. The mixture was cooled and concentrated under reduced pressure. The residue was purified by MPLC on silica eluting with 5% methanol/DCM then 15% methanol/DCM. The title compound was obtained as a colourless solid (171 mg, 75%). 1H NMR δ (d6-DMSO): 5.19 (4H, s); 5.92 (2H, s), 6.87 (1H, s); 7.28-7.48 (12H, m); 8.06 (1H, dd); 8.17 (1H, d), 8.65 (1H, s); 9.68 (1H, s); 10.85 (1H, br s); m/z (LCMS; ESI+) 469 (MH+).

후처리

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by MPLC on silica eluting with 5% methanol/DCM

출처 및 근거

ORD 기록
ord-f198ca05def7445cacb41c70095c7dc3
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07951830B2

반응 노트

불러오는 중…