Formaldehyde → (S)-7-Chloro-10-[3-(3-methoxy-propyl)-4-methyl-piperazin-1-yl]-4H-3-thia-4,9-diaza-benzo[f]azulene

HRID 131478ノート

反応式

HRID 131478 の反応式
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]2[NH:6][C:7]3[S:8][CH:9]=[CH:10][C:11]=3[C:12]([N:14]3[CH2:19][CH2:18][NH:17][C@@H:16]([CH2:20][CH2:21][CH2:22][O:23][CH3:24])[CH2:15]3)=[N:13][C:4]=2[CH:3]=1.C=O.[C:29](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]2[NH:6][C:7]3[S:8][CH:9]=[CH:10][C:11]=3[C:12]([N:14]3[CH2:19][CH2:18][N:17]([CH3:29])[C@@H:16]([CH2:20][CH2:21][CH2:22][O:23][CH3:24])[CH2:15]3)=[N:13][C:4]=2[CH:3]=1

参加物

5

反応物 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 136090412(S)-7-Chloro-10-[3-(3-methoxy-propyl)-piperazin-1-yl]-4H-3-thia-4,9-diaza-benzo[f]azulene

生成物 1

HCID 136090372(S)-7-Chloro-10-[3-(3-methoxy-propyl)-4-methyl-piperazin-1-yl]-4H-3-thia-4,9-diaza-benzo[f]azulene収率 77%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Combine (S)-7-chloro-10-[3-(3-methoxy-propyl)-piperazin-1-yl]-4H-3-thia-4,9-diaza-benzo[f]azulene (280.3 mg, 0.72 mmol), formaldehyde (64.0 μL, 0.79 mmol, 37% in water), and dichloromethane (10.0 ml). Stir the mixture at ambient temperature for 5 minutes and then add sodium triacetoxyborohydride (227.9 mg, 1.08 mmol). After stirring for 30 minutes at ambient temperature, quench the reaction with saturated sodium bicarbonate. Remove the organic portion and wash (brine), dry (sodium sulfate), and reduce the extracts to residue. Purify the residue on silica gel using a gradient of dichloromethane to dichloromethane/methanol (90:10) to give 223.0 mg (77%) of the title compound: mass spectrum (ion spray): m/z=405.1 (M+1).

後処理

  1. stirringAfter stirring for 30 minutes at ambient temperature
  2. customquench
  3. customthe reaction with saturated sodium bicarbonate
  4. customRemove the organic portion
  5. washwash (brine)
  6. dry with materialdry (sodium sulfate)
  7. customPurify the residue on silica gel using a gradient of dichloromethane to dichloromethane/methanol (90:10)

出典と根拠

ORDレコード
ord-1d801437e9944a0cb87383faac03d8e7
出典データセット
uspto-grants-2008_06
特許番号
US07384934B2

反応ノート

読み込み中…