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

HRID 983615

反応式

HRID 983615 の反応式
C(OC([N:8]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=1)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH:17][C:18]2([CH3:28])[C:27]3[N:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH2:21][CH2:20][CH2:19]2)=[CH:12][CH:11]=1)=O)(C)(C)C.N1C=CC=CC=1CNCC1C=CC(CN(CC2NC3C=CC=CC=3N=2)C2(C)C3N=CC=CC=3CCC2)=CC=1>>[N:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[CH2:29][NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][NH:17][C:18]2([CH3:28])[C:27]3[N:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH2:21][CH2:20][CH2:19]2)=[CH:14][CH:15]=1

参加物

3

反応物 2

HCID 22018594N-(2-pyridinylmethyl)-N'-(1H-benzimidazol-2-ylmethyl)-N'-(8-methyl-5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamineHCID 22018645N-tert-Butoxycarbonyl-N-(2-pyridinylmethyl)-N'-(8-methyl-5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

生成物 1

HCID 22018665N-(2-Pyridinylmethyl)-N'-(8-methyl-5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

実験手順

the intermediate from above (121 mg, 0.26 mmol) was converted to the hydrobromide salt with simultaneous deprotection of the BOC group to afford 89 mg (79%) of AMD9361 as a white solid. 1H NMR (D2O) □1.84 (s, 3H), 2.02-2.11 (m, 2H), 2.27-2.35 (m, 1H), 2.44-2.53 (m, 1H), 2.93-3.08 (m, 2H), 4.02 (d, 1H, J=12 Hz), 4.30 (d, 1H, J=12 Hz), 4.50 (s, 2H), 4.75 (s, 2H), 7.50-7.60 (m, 5H), 7.93 (dd, 1H, J=8, 1 Hz), 8.05-8.10 (m, 1H), 8.15 (d, 1H, J=8 Hz), 8.57-8.63 (m, 2H), 8.87 (br d, 1H, J=6 Hz); 13C NMR (D2O) □18.5, 25.7, 27.8, 31.2, 46.2, 47.7, 51.7, 62.6, 125.5, 128.1, 128.4, 131.3, 131.6, 133.1, 136.4, 142.2, 144.4, 145.6, 146.4, 147.1, 150.6. ES-MS m/z 373 (M+H). Anal. Calcd. for C24H28N4.4.6HBr.1.8H2O: C, 37.09; H, 4.69; N, 7.21; Br, 47.30. Found: C, 36.99; H, 4.68; N, 6.99; Br, 47.43. AMD9405: Preparation of N-(2-pyridinylmethyl)-N′-(1H-benzimidazol-2-ylmethyl)-N′-(8-methyl-5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (free base)

後処理

  1. customto afford 89 mg (79%) of AMD9361 as a white solid

出典と根拠

ORDレコード
ord-c0a5942c881b4e9b803f459e5f157c27
出典データセット
uspto-grants-2005_03
特許番号
US06864265B2

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