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

HRID 747368

반응식

HRID 747368 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.[BH3-][C:32]#[N:33].[Na+]>CO>[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]([CH2:27][NH:3][C:2]2[NH:1][CH:5]=[CH:32][N:33]=2)=[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

참가 물질

4

반응물 2

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

생성물 1

HCID 22018604(1H-benzimidazol-2-ylmethyl)-{4-[(1H-imidazol-2-ylamino)-methyl]-benzyl}-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine수율 19.4%

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 (200 mg, 0.49 mmol) and the amine (41 mg, 0.49 mmol) from above in MeOH (5 mL) was added NaBH3CN (94.3 mg, 1.5 mmol) and the mixture was stirred at room temperature for 5 days. Purification of the crude yellow foam by column chromatography on silica gel (100:1:1—CH2Cl2:MeOH:NH4OH) afforded AMD9741 (26 mg, 15%) as a brown solid (22mg, 10%). 1H NMR (CDCl3) δ 1.61-1.76 (m, 1H), 1.92-2.09 (m, 2H), 2.17-2.27 (m, 1H), 2.68-2.76 (m, 1H), 2.80-2.90 (m, 1H), 3.64 (s, 2H), 3.89 (d, 1H, J=16.5 Hz), 4.05-4.14 (m, 2H), 4.22 (s, 2H), 4.39 (br s, 1H), 6.54 (s, 2H), 7.06 (d, 2H, J=7.8 Hz), 7.15-7.20 (m, 3H), 7.25 (d, 2H, J=6.9 Hz), 7.43 (d, 1H, J=7.8 Hz), 7.54 (br s, 2H), 8.67 (d, 1H, J=4.5 Hz); 13C NMR (CDCl3) δ 19.22, 21.83, 27.12, 45.73, 46.41, 51.49, 58.49, 111.83, 112.90, 115.59, 119.64, 120.29, 125.33, 126.71, 132.76, 135.33, 135.86, 136.22, 144.75, 148.75, 154.19, 155.23. ES-MS m/z 464.3 (M+H). Anal. Calcd. for C28H29N7.1.4CH2Cl2: C, 60.62; H, 5.50; N, 16.83. Found: C, 60.53; H, 5.48; N, 16.94.

후처리

  1. customPurification of the crude yellow foam by column chromatography on silica gel (100:1:1—CH2Cl2:MeOH:NH4OH)

출처 및 근거

ORD 기록
ord-c0f9d04e42e54645ace7eed66a4a1039
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07396840B2

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