N,O-Dimethylhydroxylamine → HCID 86639885、化合物

HRID 1908860ノート

反応式

HRID 1908860 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 86639885HCID 86639885、化合物収率 86.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5b3dd4ff64aa47b99e306a37cbe5a763
出典データセット
uspto-grants-2013_12
特許番号
US08598208B2

反応ノート

読み込み中…