HCID 86691397、化合物 → N-[2-(1,1-Dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-yl]-2-methylalaninamide

HRID 540168ノート

反応式

HRID 540168 の反応式
[N:1]([C:4]([CH3:33])([CH3:32])[C:5]([NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH3:18])[CH:16]=2)[N:11]=[C:10]([N:19]2[CH2:25][C:24]3[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=3[S:22](=[O:31])(=[O:30])[CH2:21][CH2:20]2)[CH:9]=1)=[O:6])=[N+]=[N-]>C(OCC)(=O)C.[Pd]>[O:31]=[S:22]1(=[O:30])[C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[CH2:25][N:19]([C:10]2[CH:9]=[C:8]([NH:7][C:5](=[O:6])[C:4]([CH3:33])([CH3:32])[NH2:1])[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([CH3:18])[CH:16]=3)[N:11]=2)[CH2:20][CH2:21]1

参加物

4

反応物 1

HCID 86691397HCID 86691397、化合物

生成物 1

HCID 71254805N-[2-(1,1-Dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-yl]-2-methylalaninamide収率 73%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution 2-azido-N-[2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-yl]-2-methylpropanamide (160 mg, 0.345 mmol) in ethyl acetate (25 mL) was added 10% palladium on carbon (100 mg), the flask was degassed and refilled with hydrogen (repeated for three times). After being stirred at room temperature overnight under a hydrogen atmosphere, the resulting mixture was filtered. The filtrate was concentrated in vacuo. The residue was purified by flash chromatography to afford 110 mg of the title compound (yield was 73%). MS obsd. (ESI+) [(M+H)+] 439, 1H NMR (400 MHz, CDCl3) δ ppm 11.05 (s, 1 H), 8.30 (s, 1 H), 8.02 (dd, J=0.8, 7.6 Hz, 1 H), 7.89 (d, J=7.2 Hz, 1 H), 7.59 (d, J=8.8 Hz, 1 H), 7.53 (t, J=7.6 Hz, 1 H), 7.37 (m, 3 H), 5.17 (s, 2 H), 4.6 (brs., 2 H), 3.56 (s, 2 H), 2.48 (s, 3 H), 1.56 (s, 6 H).

後処理

  1. customthe flask was degassed
  2. additionrefilled with hydrogen (repeated for three times)
  3. filtrationthe resulting mixture was filtered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-6b5dabad80b4400c80a99452f72620c8
出典データセット
uspto-grants-2014_10
特許番号
US08871756B2

反応ノート

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