2-Aminobenzimidazole → {4-[(1H-Benzimidazol-2-ylamino)-methyl]-benzyl}-(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine

HRID 7183

反応式

HRID 7183 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]([CH2:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=1)[CH:12]1[C:21]2[N:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:15][CH2:14][CH2:13]1.[NH2:31][C:32]1[NH:33][C:34]2[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=2[N:36]=1.[BH3-]C#N.[Na+]>CO>[NH:33]1[C:34]2[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=2[N:36]=[C:32]1[NH:31][CH2:27][C:26]1[CH:29]=[CH:30][C:23]([CH2:22][N:11]([CH2:10][C:2]2[NH:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:1]=2)[CH:12]2[C:21]3[N:20]=[CH:19][CH:18]=[CH:17][C:16]=3[CH2:15][CH2:14][CH2:13]2)=[CH:24][CH:25]=1

参加物

5

反応物 3

HCID 136242-AminobenzimidazoleHCID 5003444Sodium cyanoborohydrideHCID 219849824-{[(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzaldehyde

生成物 1

HCID 22018650{4-[(1H-Benzimidazol-2-ylamino)-methyl]-benzyl}-(1H-benzimidazol-2-ylmethyl)-(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 A: To a stirred solution of 4-{[(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzaldehyde (140 mg, 0.34 mmol) and 2-aminobenzimidazole (45 mg, 0.0.34 mmol) in MeOH (4 mL) was added NaBH3CN (64 mg, 1.1 mmol) and the mixture was stirred at room temperature for 20 hours. Purification of the crude yellow foam by column chromatography on silica gel (200:1:1—EtOAc:MeOH:NH4OH) followed by radial chromatography on silica gel (100:1:1—CH2Cl2:MeOH:NH4OH) afforded AMD9693 (26 mg, 15%) as a white solid. 1H NMR (CDCl3) δ 1.57–1.74 (m, 1H), 1.87–2.05 (m, 2H), 2.10–2.20 (m, 1H), 2.63–2.75 (m, 1H), 2.75–2.90 (m, 1H), 3.54 (s, 2H), 3.86 (d, 1H, J=16.8 Hz), 4.03–4.16 (m, 2H), 4.24–4.35 (m, 2H), 5.44 (br s, 1H), 6.88–6.91 (m, 4H), 7.10–7.19 (m, 7H), 7.42 (d, 1H, J=7.5 Hz), 7.54 (br s, 2H), 8.65 (d, 1H, J=4.2 Hz); 13C NMR (CDCl3) δ 21.16, 24.26, 29.10, 46.66, 48.40, 53.29, 60.62, 111.39 (br), 118.11 (br), 120.13, 121.81, 122.37, 127.22, 128.57, 133.86, 134.79, 137.41, 138.17, 143.78, 146.67, 155.56, 156.41, 157.20. ES-MS m/z 514.4 (M+H). Anal. Cald. for C32H31N7.0.8CH2Cl2.0.4C4H8O2: C, 66.98; H, 5.85; N, 15.90. Found: C, 67.14; H, 5.66; N, 15.87.

後処理

  1. customPurification of the crude yellow foam by column chromatography on silica gel (200:1:1—EtOAc:MeOH:NH4OH)
  2. customafforded AMD9693 (26 mg, 15%) as a white solid

出典と根拠

ORDレコード
ord-1bf96c7fefb149cc8ee915c4ce2cbeca
出典データセット
uspto-grants-2006_08
特許番号
US07084155B2

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