Sodium triacetoxyborohydride → N-(5-butyl-2-pyridinylmethyl)-N'-(1H-benzimidazol-2-ylmethyl)-N'-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

HRID 7142

反応式

HRID 7142 の反応式
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]([CH:21]1[C:30]2[N:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH2:24][CH2:23][CH2:22]1)[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][NH2:20])=[CH:15][CH:14]=1.[CH2:31]([C:35]1[CH:36]=[CH:37][C:38]([CH:41]=O)=[N:39][CH:40]=1)[CH2:32][CH2:33][CH3:34].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH2:31]([C:35]1[CH:36]=[CH:37][C:38]([CH2:41][NH:20][CH2:19][C:16]2[CH:15]=[CH:14][C:13]([CH2:12][N:11]([CH2:10][C:2]3[NH:3][C:4]4[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=4[N:1]=3)[CH:21]3[C:30]4[N:29]=[CH:28][CH:27]=[CH:26][C:25]=4[CH2:24][CH2:23][CH2:22]3)=[CH:18][CH:17]=2)=[N:39][CH:40]=1)[CH2:32][CH2:33][CH3:34]

参加物

5

反応物 3

HCID 5049666Sodium triacetoxyborohydrideHCID 213962665-n-Butylpyridine-2-carboxaldehydeHCID 21985008N-[(1H-Benzo[d]imidazol-2-yl)methyl]-N-(4-(aminomethyl)-benzyl)-5,6,7,8-tetrahydroquinolin-8-amine

生成物 1

HCID 22018809N-(5-butyl-2-pyridinylmethyl)-N'-(1H-benzimidazol-2-ylmethyl)-N'-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Using general procedure B: N-(1H-benzimidazol-2-ylmethyl)-N-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (0.1258 g, 0.316 mmol) and 5-n-butylpyridine-2-carboxaldehyde (0.0603 g, 0.294 mmol) were reacted with NaBH(OAc)3 (0.0942 g, 0.444 mmol) in CH2Cl2 (2.5 mL). Purification of the crude material by radial chromatography (2 mm TLC plate, 50:1:1 CH2Cl2: CH3OH: NH4OH) provided 0.0713 g (45%) of AMD9398 (free base).

後処理

  1. customPurification of the crude material by radial chromatography (2 mm TLC plate, 50:1:1 CH2Cl2: CH3OH: NH4OH)
  2. customprovided 0.0713 g (45%) of AMD9398 (free base)

出典と根拠

ORDレコード
ord-b8796c8cf3334b43b0cdd5ad9d83bed5
出典データセット
uspto-grants-2006_08
特許番号
US07084155B2

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