Benzaldehyde → 2-Benzyl-1,2,3,4-tetrahydro-isoquinoline-3(S)-carboxylic acid {2-[3-(4-cyanobenzyl)-3H-imidazol-4-yl]-ethyl}-amide

HRID 1584270ノート

反応式

HRID 1584270 の反応式
Cl.[C:2]([C:4]1[CH:30]=[CH:29][C:7]([CH2:8][N:9]2[C:13]([CH2:14][CH2:15][NH:16][C:17]([C@@H:19]3[CH2:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:21][NH:20]3)=[O:18])=[CH:12][N:11]=[CH:10]2)=[CH:6][CH:5]=1)#[N:3].CCN(CC)CC.[CH:38](=O)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C([BH3-])#N.[Na+]>CO>[C:2]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]2[C:13]([CH2:14][CH2:15][NH:16][C:17]([C@@H:19]3[CH2:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:21][N:20]3[CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[O:18])=[CH:12][N:11]=[CH:10]2)=[CH:29][CH:30]=1)#[N:3]

参加物

6

反応物 4

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 701220621,2,3,4-Tetrahydro-isoquinoline-3(S)-carboxylic acid {2-[3-(4-cyanobenzyl)-3H-imidazol-4-yl]-ethyl}-amide hydrochloride

生成物 1

HCID 154109492-Benzyl-1,2,3,4-tetrahydro-isoquinoline-3(S)-carboxylic acid {2-[3-(4-cyanobenzyl)-3H-imidazol-4-yl]-ethyl}-amide

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

1,2,3,4-Tetrahydro-isoquinoline-3(S)-carboxylic acid {2-[3-(4-cyanobenzyl)-3H-imidazol-4-yl]-ethyl}-amide hydrochloride (0.15 g, 0.33 mmol) was dissolved in MeOH (7 mL). Et3N was added to this solution dropwise until the pH=5. To the solution was added benzaldehyde (0.069 mL, 0.65 mmol) and sodium cyanoborohydride (0.041 g, 0.65 mmol). After stirring for 18 hr. the mixture was evaporated in vacuo and the residue was partitioned between EtOAc (50 mL) and saturated NaHCO3 (30 mL). The organic layer was washed with saturated NaCl solution (30 mL) and dried (MgSO4). Filtration and concentration to dryness gave the title compound after purification on silica gel eluting with CH2Cl2 :

後処理

  1. customthe mixture was evaporated in vacuo
  2. customthe residue was partitioned between EtOAc (50 mL) and saturated NaHCO3 (30 mL)
  3. washThe organic layer was washed with saturated NaCl solution (30 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationFiltration and concentration to dryness

出典と根拠

ORDレコード
ord-6e4e5af36b64422fbe13a26b6ed0ca6e
出典データセット
uspto-grants-1999_08
特許番号
US05932590

反応ノート

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