Triethylamine → 4-(5-Bromopyridin-2-yl)-1,4-diazepan-2-one

HRID 2207341노트

반응식

HRID 2207341 반응식
[Br:1][C:2]1[CH:3]=[N:4][C:5](F)=[CH:6][CH:7]=1.[NH:9]1[CH2:15][CH2:14][CH2:13][NH:12][CH2:11][C:10]1=[O:16].C(N(CC)CC)C>CN(C)C(=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:12]2[CH2:13][CH2:14][CH2:15][NH:9][C:10](=[O:16])[CH2:11]2)=[N:4][CH:3]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 27831685-Bromo-2-fluoropyridineHCID 134285321,4-Diazepan-2-one

생성물 1

HCID 647225474-(5-Bromopyridin-2-yl)-1,4-diazepan-2-one

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 31374Dimethylacetamide용매

실험 절차

A solution of 3-bromo-6-fluoropyridine (315 mg, 1.79 mmol), 1,4-diazepan-2-one (200 mg, 1.75 mmol), and triethylamine (0.269 ml, 1.93 mmol) in N,N-dimethylacetamide (3 mL) was irradiated in a microwave reactor for twenty minutes at 220° C. The reaction mixture was diluted with ethyl acetate (35 mL) and then washed with saturated aqueous sodium bicarbonate (15 mL), water (3×10 mL), and brine (15 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (0.5-8.5% methanol/dichloromethane) to afford 4-(5-bromopyridin-2-yl)-1,4-diazepan-2-one. MS ESI calc'd. for C10H13BrN3O [M+H]+ 270 and 272. found 270 and 272. 1H NMR (500 MHz, DMSO-d6): δ 8.14 (d, J=2.4 Hz, 1H), 7.68 (dd, J=9.1, 2.7 Hz, 1H), 7.48 (m, 1H), 6.70 (d, J=9.1 Hz, 1H), 4.11 (s, 2H), 3.85 (s, 2H), 3.18 (m, 2H), 1.62 (m, 2H).

후처리

  1. washwashed with saturated aqueous sodium bicarbonate (15 mL), water (3×10 mL), and brine (15 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by chromatography on silica gel (0.5-8.5% methanol/dichloromethane)

출처 및 근거

ORD 기록
ord-826abac64754418ab8373702dfe5b108
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09376418B2

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