Sodium triacetoxyborohydride → pyridine-2-sulfonic acid 4-({(5,6,7,8-tetrahydro-quinolin-8-yl)-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-ylmethyl]-amino}-methyl)-benzylamide

HRID 2308304

Reaktionsgleichung

Reaktionsgleichung von HRID 2308304
[N:1]1[C:10]2[CH:9]([NH:11][CH2:12][C:13]3[CH:29]=[CH:28][C:16]([CH2:17][NH:18][S:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=4)(=[O:21])=[O:20])=[CH:15][CH:14]=3)[CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:30][Si:31]([CH3:48])([CH3:47])[CH2:32][CH2:33][O:34][CH2:35][N:36]1[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=2[N:38]=[C:37]1[CH:45]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[N:1]1[C:10]2[CH:9]([N:11]([CH2:12][C:13]3[CH:14]=[CH:15][C:16]([CH2:17][NH:18][S:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=4)(=[O:20])=[O:21])=[CH:28][CH:29]=3)[CH2:45][C:37]3[N:36]([CH2:35][O:34][CH2:33][CH2:32][Si:31]([CH3:30])([CH3:47])[CH3:48])[C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=4[N:38]=3)[CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Komponenten

4

Edukt 3

HCID 5049666Sodium triacetoxyborohydrideHCID 10179646Pyridine-2-sulfonic acid 4-[(5,6,7,8-tetrahydro-quinolin-8-ylamino)-methyl]-benzylamideHCID 120171281-(2-Trimethylsilylethoxymethyl)-2-formyl-benzimidazole

Produkt 1

HCID 68896453pyridine-2-sulfonic acid 4-({(5,6,7,8-tetrahydro-quinolin-8-yl)-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-ylmethyl]-amino}-methyl)-benzylamideAusbeute 41 %

Versuchsvorschrift

Using general procedure B: Reaction of pyridine-2-sulfonic acid 4-[(5,6,7,8-tetrahydro-quinolin-8-ylamino)-methyl]-benzylamide (AMD9426) (150 mg, 0.37 mmol), 1-(2-trimethylsilanyl-ethoxymethyl)-1 H-benzoimidazole-2-carbaldehyde (102 mg, 0.37 mmol), and NaBH(OAc)3 (233 mg, 1.10 mmol) for 1 h at room temperature followed by column chromatography on silica gel (CH2Cl2/MeOH/NH4OH 198:1:1) gave the title compound (101 mg, 41%) as a yellow foam. 1H NMR (300 MHz, CD3OD) δ 0.00 (s, 9H), 0.75 (dd, 2H, J=8.1, 8.1 Hz), 1.58-1.75 (m, 2H), 2.22 (br s, 2H), 2.66-2.85 (m, 2H), 3.25 (dd, 2H, J=8.1, 8.1 Hz), 3.66 (d, 1H, J=14.1 Hz), 3.78 (d, 1H, J=14.1 Hz), 4.02 (d, 1H, J=6.0 Hz), 4.06-4.16 (m, 1H) 4.20 (brs, 2H), 4.81 (br s, 1H), 5.68 (d, 1H, J=12.0 Hz), 5.91 (d, 1H, J=12.0 Hz), 6.92 (d, 2H, J=7.8 Hz), 7.06 (dd, 1H, J=7.5, 4.8 Hz), 7.17-7.23 (m, 4H), 7.30-7.35 (m, 2H), 7.45 (ddd, 1H, J=7.5, 4.5, 1.1 Hz), 7.61-7.64 (m, 1H), 7.87 (ddd, 1H, J=7.8, 7.8,1.7 Hz), 7.98 (d, 1H, J=7.8 Hz), 8.55 (d, 1H, J=3.6 Hz), 8.68 (d, 1H, J=3.9 Hz).ES-MS m/z 669 (M+H).

Quellen und Nachweise

ORD-Eintrag
ord-424ecc1b03114a348b781d9af36cf924
Quelldatensatz
uspto-grants-2004_12
Patentnummer
US06835731B2

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