Sodium triacetoxyborohydride → N-Pyridin-2-ylmethyl-4-({(5,6,7,8-tetrahydro-quinolin-8-yl)-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazol-2-ylmethyl]-amino}-methyl)-benzenesulfonamide

HRID 970897

Reaction equation

HRID 970897 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([CH2:18][NH:19][CH:20]2[C:29]3[N:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH2:23][CH2:22][CH2:21]2)=[CH:14][CH:13]=1)(=[O:11])=[O:10].[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[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][S:9]([C:12]1[CH:13]=[CH:14][C:15]([CH2:18][N:19]([CH:20]2[C:29]3[N:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH2:23][CH2:22][CH2:21]2)[CH2:45][C:37]2[N:36]([CH2:35][O:34][CH2:33][CH2:32][Si:31]([CH3:30])([CH3:47])[CH3:48])[C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=3[N:38]=2)=[CH:16][CH:17]=1)(=[O:10])=[O:11]

Participants

4

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 10136157HCID 10136157, compoundHCID 120171281-(2-Trimethylsilylethoxymethyl)-2-formyl-benzimidazole

Product 1

HCID 68899533N-Pyridin-2-ylmethyl-4-({(5,6,7,8-tetrahydro-quinolin-8-yl)-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazol-2-ylmethyl]-amino}-methyl)-benzenesulfonamideYield 50%

Procedure

Using general procedure B: Reaction of N-pyridin-2-ylmethyl-4-[(5,6,7,8-tetrahydro-quinolin-8-ylamino)-methyl]-benzenesulfonamide (97 mg, 0.24 mmol), 1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazole-2-carbaldehyde (72 mg, 0.26 mmol), and NaBH(OAc)3 (151 mg, 0.71 mmol) for 1 h at room temperature followed by column chromatography on silica gel (CH2Cl2/MeOH/NH4OH 98:1:1) gave the title compound (63 mg, 50%) as a white foam. 1H NMR (300 MHz, CDCl3) δ 0.00 (s, 9H), 0.77 (dd, 2H, J=7.5, 7.5 Hz), 1.73-1.74 (m, 1H), 1.95-2.06 (m, 2H), 2.20-2.25 (m, 1H), 2.66-2.86 (m, 2H), 3.29-3.35 (m, 2H), 3.78 (d, 1H, J=14.7 Hz), 3.98 (d, 1H, J=14.7 Hz), 4.05 (dd, 1H, J=9.3, 6.3 Hz), 4.13 (d, 2H, J=6.0 Hz), 4.18 (brs, 2H), 5.70 (d, 1H, J=12.0 Hz), 5.98 (d, 1H, J=12.0 Hz), 7.06-7.10 (m, 2H), 7.13-7.18 (m, 3H), 7.31-7.36 (m, 2H), 7.43 (d, 2H, J=8.1 Hz), 7.52-7.66 (m, 4H), 8.42 (d, 1H, J=4.8 Hz), 8.52 (d, 1H, J=4.5 Hz).

Sources & evidence

ORD record
ord-052c528a791f4de6a447d5d4d63e3b6d
Source dataset
uspto-grants-2007_12
Patent number
US07312234B2

Linked notes

Loading…