Indole-3-Carboxaldehyde → (1H-benzimidazol-2-ylmethyl)-(4-{[(1H-indol-3-ylmethyl)-amino]-methyl}-benzyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine

HRID 747362

反応式

HRID 747362 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=O)=[CH:2]1.[NH:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[C:13]1[CH2:21][N:22]([CH:32]1[C:41]2[N:40]=[CH:39][CH:38]=[CH:37][C:36]=2[CH2:35][CH2:34][CH2:33]1)[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][NH2:31])=[CH:26][CH:25]=1.[BH4-].[Na+]>CO>[NH:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[C:13]1[CH2:21][N:22]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][NH:31][CH2:10][C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)=[CH:26][CH:25]=1)[CH:32]1[C:41]2[N:40]=[CH:39][CH:38]=[CH:37][C:36]=2[CH2:35][CH2:34][CH2:33]1

参加物

5

反応物 3

HCID 10256Indole-3-CarboxaldehydeHCID 4311764Sodium borohydrideHCID 21985008N-[(1H-Benzo[d]imidazol-2-yl)methyl]-N-(4-(aminomethyl)-benzyl)-5,6,7,8-tetrahydroquinolin-8-amine

生成物 1

HCID 22018789(1H-benzimidazol-2-ylmethyl)-(4-{[(1H-indol-3-ylmethyl)-amino]-methyl}-benzyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Using General Procedure B: 1H-Indole-3-carbaldehyde (73 mg, 0.50 mmol) and N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (200 mg, 0.50 mmol) were stirred at 40° C. in MeOH (5 mL) for 4 hours. NaBH4 (38 mg, 1.0 mmol) was added and the resultant mixture stirred at room temperature for an additional 15 minutes. Purification of the crude white foam by column chromatography on silica gel (200:1:1—EtOAc:MeOH:NH4OH) afforded AMD9673 (80 mg, 31%) as a white foam. 1H NMR (CDCl3) δ 1.59-1.75 (m, 1H), 1.81-2.09 (m, 2H), 2.16-2.30 (m, 1H), 2.64-2.76 (m, 1H), 2.76-2.91 (m, 1H), 3.69 (s, 2H), 3.78 (s, 2H), 3.92-3.98 (m, 3H), 4.04-4.09 (m, 1H), 4.15 (d, 1H, J=16.5 Hz), 7.02-7.07 (m, 2H), 7.11-7.21 (m, 6H), 7.25-7.34 (m, 3H), 7.41 (d, 1H, J=7.2 Hz), 7.54-7.57 (m, 3H), 8.68 (d, 1H, J=3.9 Hz), 8.75 (br s, 1H); 13C NMR (CDCl3) δ 21.74, 23.88, 29.60, 44.05, 48.89, 52.95, 54.06, 60.72, 111.68, 113.70, 119.08, 119.77, 121.97, 122.30, 122.66, 123.71, 127.40, 128.84, 129.07, 135.15, 136.70, 137.66, 138.60 (2 carbons), 147.27, 156.70, 157.79. ES-MS m/z 532.4 (M—C9H8N). Anal. Calcd. for C34H34N6.0.7H2O.0.2CH2Cl2: C, 73.84; H, 6.49; N, 15.11. Found: C, 73.95; H, 6.60; N, 14.81.

後処理

  1. customPurification of the crude white foam by column chromatography on silica gel (200:1:1—EtOAc:MeOH:NH4OH)
  2. customafforded AMD9673 (80 mg, 31%) as a white foam

出典と根拠

ORDレコード
ord-9b22547c902c41cca765f84c13a4038a
出典データセット
uspto-grants-2008_07
特許番号
US07396840B2

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