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Potassium Carbonate → 4-(((1H-Benzimidazol-2-ylmethyl)(5,6,7,8-tetrahydroquinolin-8-yl)amino)methyl)-N-(pyridin-2-yl)benzamide

HRID 970889
ノート
印刷プレビュー

反応式

HRID 970889 の反応式
C([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:17]Cl)(OC(C)(C)C)=O.[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH:25][C:26](=[O:45])[C:27]1[CH:32]=[CH:31][C:30]([CH2:33][NH:34][CH:35]2[C:44]3[N:43]=[CH:42][CH:41]=[CH:40][C:39]=3[CH2:38][CH2:37][CH2:36]2)=[CH:29][CH:28]=1.C([O-])([O-])=O.[K+].[K+]>CC#N.C(OCC)(=O)C>[CH2:37]1[CH2:38][C:39]2[CH:40]=[CH:41][CH:42]=[N:43][C:44]=2[CH:35]([N:34]([CH2:17][C:9]2[NH:8][C:12]3[C:11](=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:10]=2)[CH2:33][C:30]2[CH:31]=[CH:32][C:27]([C:26]([NH:25][C:20]3[N:19]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:45])=[CH:28][CH:29]=2)[CH2:36]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 10133044HCID 10133044、化合物HCID 15829159tert-Butyl 2-(chloromethyl)-1H-benzimidazole-1-carboxylate

生成物 1

HCID 98055134-(((1H-Benzimidazol-2-ylmethyl)(5,6,7,8-tetrahydroquinolin-8-yl)amino)methyl)-N-(pyridin-2-yl)benzamide収率 47.6%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

N-BOC-chloromethylbenzimidazole (115 mg, 0.43 mmol), N-Pyridin-2-yl-4-[(5,6,7,8-tetrahydro-quinolin-8-ylamino)methyl]-benzamide (AMD9362) (155 mg, 0.43 mmol), and K2CO3 (179 mg, 1.29 mmol) were heated to reflux in CH3CN (3 mL) for 24 hours under N2. The reaction mixture was diluted with 200 mL ethyl acetate, and washed with sat. NaHCO3, brine and dried over Na2SO4. Evaporation of the solvent and purification of the residue by flash chromatography on silica gel, followed by radial chromatography on silica gel (2 mm plate, 3:3:94 CH3OH—NH3 H2O—CH2Cl2), afforded AMD9370 (100 mg, 47%) as white foam. 1H NMR (CDCl3) δ 1.68-1.75 (m, 1H), 1.97-2.08 (m, 2H), 2.26-2.32 (m, 1H), 2.71-2.84 (m, 1H), 2.86-2.91 (m, 1H), 3.84 (s, 2H), 3.95 (d, 1H, J=16.5 Hz), 4.08-4.14 (m, 1H), 4.22 (d, 1H, J=16.0 Hz), 7.03-7.07 (m, 1H), 7.16-7.22 (m, 3H), 7.45 (d, 1H, J=6.9 Hz), 7.52-7.61 (m, 3H), 7.65 (d, 1H, J=7.5 Hz), 7.73 (ddd, 1H, J=1.8, 7.2, 8.7 Hz), 7.80 (d, 2H, J=8.1 Hz), 8.27-8.29 (m, 1H), 8.33 (d 1H, J=8.4 Hz), 8.44 (br, s, 1H), 8.72-8.80 (m, 1H); 13C NMR (CDCl3) δ 21.72, 23.30, 29.56, 49.29, 54.16, 60.83, 111.39, 114.52, 120.17, 122.29, 122.81, 127.72, 129.28, 133.58, 135.17, 137.76, 138.77, 144.61, 147.38, 148.21, 152.00, 156.13, 157.54, 165.99; ES-MS m/z 489.2 (M+H); Anal. Calcd. for (C30H28N6O).0.6(H2O).0.7(CHCl3): C, 63.25; H, 5.17; N, 14.42. Found: C, 63.56; H, 5.25; N, 14.31.

後処理

  1. washwashed with sat. NaHCO3, brine
  2. dry with materialdried over Na2SO4
  3. customEvaporation of the solvent and purification of the residue by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-8ef50aee025f4ab0a571c05d0003ce8a
出典データセット
uspto-grants-2007_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07312234B2

反応ノート

読み込み中…

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