HCID 15409145、化合物 → HCID 15409146、化合物

HRID 1416239ノート

反応式

HRID 1416239 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([N:13]3[CH2:18][CH2:17][N:16]([C:19]4[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=4)[CH2:15][CH2:14]3)=O)[N:10]=2)[CH:7]=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11][N:13]3[CH2:18][CH2:17][N:16]([C:19]4[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=4)[CH2:15][CH2:14]3)[N:10]=2)[CH:7]=1

参加物

3

反応物 1

HCID 15409145HCID 15409145、化合物

生成物 1

HCID 15409146HCID 15409146、化合物収率 15.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To 1-[(6-chloroimidazo[1,2-a]pyridin-2-yl)carbonyl]-4-(4-methoxy-phenyl)piperazine (0.182 g) in THF (6 mL) is added borane-methyl sulfide complex (Aldrich; 0.14 mL). Additional THF (4 mL) is added and the mixture is stirred overnight, after which it is quenched with the dropwise addition of methanol. The mixture is concentrated under reduced pressure and then acetone/6N HCl (10/1) is added. The resulting mixture is stirred for 40 min and then concentrated under reduced pressure. The residue is partitioned between dichloromethane and aq. sodium bicarbonate. The organic layers are filtered through sodium sulfate, concentrated, and the residue chromatographed on silica gel using methanol/dichloromethane (2/98 to 4/96) to give 0.027 g of the title compound; mp 111-112° C.; IR (mineral oil) 1512, 1254, 1498, 1035, 830 cm-1. 1H NMR (CDCl3) δ2.74, 3.13, 3.76, 3.77, 6.82, 6.90, 7.12, 7.52, 7.54, 8.13.

後処理

  1. customafter which it is quenched with the dropwise addition of methanol
  2. concentrationThe mixture is concentrated under reduced pressure
  3. additionacetone/6N HCl (10/1) is added
  4. stirringThe resulting mixture is stirred for 40 min
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is partitioned between dichloromethane and aq. sodium bicarbonate
  7. filtrationThe organic layers are filtered through sodium sulfate
  8. concentrationconcentrated
  9. customthe residue chromatographed on silica gel

出典と根拠

ORDレコード
ord-2599795742fe44b7b4561b060ae289c3
出典データセット
uspto-grants-1999_06
特許番号
US05912246

反応ノート

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