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

HRID 7183

반응식

HRID 7183 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 22018650{4-[(1H-Benzimidazol-2-ylamino)-methyl]-benzyl}-(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1bf96c7fefb149cc8ee915c4ce2cbeca
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084155B2

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