Sodium triacetoxyborohydride → n-(3-Chloro-5-(trifluoromethyl)-2-pyridinylmethyl)-n'-(1h-benzimidazol-2-ylmethyl)-n'-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

HRID 7158

反応式

HRID 7158 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.[Cl:31][C:32]1[C:33]([CH:42]=O)=[N:34][CH:35]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:37]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[Cl:31][C:32]1[C:33]([CH2:42][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:34][CH:35]=[C:36]([C:38]([F:40])([F:39])[F:41])[CH:37]=1

参加物

5

反応物 3

HCID 5049666Sodium triacetoxyborohydrideHCID 21985008N-[(1H-Benzo[d]imidazol-2-yl)methyl]-N-(4-(aminomethyl)-benzyl)-5,6,7,8-tetrahydroquinolin-8-amineHCID 220187903-Chloro-5-(trifluoromethyl)picolinaldehyde

生成物 1

HCID 22018690n-(3-Chloro-5-(trifluoromethyl)-2-pyridinylmethyl)-n'-(1h-benzimidazol-2-ylmethyl)-n'-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine収率 26%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Using General Procedure B: To a stirred solution of N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (133 mg, 0.34 mmol) and 3-chloro-5-(trifluoromethyl)-pyridine-2-carboxaldehyde (66 mg, 0.32 mmol) in CH2Cl2 (5 mL) was added NaBH(OAc)3 (93 mg, 0.44 mmol) and the mixture was stirred at room temperature for 16 h. Purification of the crude material by radial chromatography on silica gel (1 mm plate, CH2Cl2/MeOH/NH4OH, 75:1:1) afforded the desired amine (48 mg, 26%) as a yellow foam.

後処理

  1. customPurification of the crude material by radial chromatography on silica gel (1 mm plate, CH2Cl2/MeOH/NH4OH, 75:1:1)

出典と根拠

ORDレコード
ord-a6b46ff1aa0f44429113e55ed89eb2bc
出典データセット
uspto-grants-2006_08
特許番号
US07084155B2

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