N,O-Dimethylhydroxylamine → HCID 86639885, 화합물

HRID 1908860노트

반응식

HRID 1908860 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH2:11][CH:12]([CH3:14])[CH3:13])[N:10]=1)[C:5](O)=[O:6].CCN(C(C)C)C(C)C.CN([C:27]([O:31][N:32]1N=NC2C=CC=C[C:33]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CNOC>C(Cl)Cl>[CH2:11]([C:9]1[CH:8]=[C:4]([CH:3]=[C:2]([CH3:1])[N:10]=1)[C:5]([N:32]([O:31][CH3:27])[CH3:33])=[O:6])[CH:12]([CH3:14])[CH3:13]

참가 물질

6

반응물 4

HCID 14232N,O-DimethylhydroxylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 574372032-Methyl-6-(2-methyl-propyl)-isonicotinic acid

생성물 1

HCID 86639885HCID 86639885, 화합물수율 86.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 2-methyl-6-(2-methyl-propyl)-isonicotinic acid (3.80 g, 16.5 mmol) in DCM (50 mL), DIPEA (10.7 g, 82.7 mmol) followed by TBTU (6.37 g, 19.9 mmol) is added. The mixture is stirred at rt for 10 min before N,O-dimethylhydroxylamine (1.94 g, 19.9 mmol) is added. The mixture is stirred at rt for 1 h before it is diluted with DCM, washed with sat. aq. NaHCO3, followed by water, dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silic gel eluting with heptane:EA 1:1 to give 2-isobutyl-N-methoxy-6,N-dimethyl-isonicotinamide (3.37 g) as a colourless oil; LC-MS: tR=0.61 min; 1H NMR (CDCl3): δ 0.95 (d, J=6.8 Hz, 6H), 2.06-2.18 (m, 1H), 2.60 (s, 3H), 2.69 (d, J=7.3 Hz, 2H), 3.37 (s, 3H), 3.57 (s, 3H), 7.13 (s, 1H), 7.18 (s, 1H).

후처리

  1. additionis added
  2. additionis added
  3. washwashed with sat. aq. NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product is purified by CC on silic gel
  8. washeluting with heptane:EA 1:1

출처 및 근거

ORD 기록
ord-5b3dd4ff64aa47b99e306a37cbe5a763
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598208B2

반응 노트

불러오는 중…