Sodium cyanoborohydride → 5-(2-{4-[6-(1H-Tetrazol-1-yl)-1,2,3,4-tetrahydronaphthalen-2-yl]piperazin-1-yl}ethyl)-2,1,3-benzoxadiazole

HRID 1519586Notes

Reaction equation

HRID 1519586 reaction equation
Cl.[N:2]1([CH2:8][CH2:9][C:10]2[CH:18]=[CH:17][C:13]3=[N:14][O:15][N:16]=[C:12]3[CH:11]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[N:19]1([C:24]2[CH:25]=[C:26]3[C:31](=[CH:32][CH:33]=2)[CH2:30][C:29](=O)[CH2:28][CH2:27]3)[CH:23]=[N:22][N:21]=[N:20]1.C([BH3-])#N.[Na+]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[N:19]1([C:24]2[CH:25]=[C:26]3[C:31](=[CH:32][CH:33]=2)[CH2:30][CH:29]([N:5]2[CH2:6][CH2:7][N:2]([CH2:8][CH2:9][C:10]4[CH:18]=[CH:17][C:13]5=[N:14][O:15][N:16]=[C:12]5[CH:11]=4)[CH2:3][CH2:4]2)[CH2:28][CH2:27]3)[CH:23]=[N:22][N:21]=[N:20]1

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 675172976-(1H-Tetrazol-1-yl)-3,4-dihydronaphthalen-2(1H)-oneHCID 675173995-(2-Piperazin-1-ylethyl)-2,1,3-benzoxadiazole hydrochloride

Product 1

HCID 680718845-(2-{4-[6-(1H-Tetrazol-1-yl)-1,2,3,4-tetrahydronaphthalen-2-yl]piperazin-1-yl}ethyl)-2,1,3-benzoxadiazole

Reagents, catalysts & solvents 1

HCID 11026Titanium isopropoxideCatalyst

Procedure

To a flask charged with 5-(2-piperazin-1-ylethyl)-2,1,3-benzoxadiazole hydrochloride (25 mg, 0.093 mmol) and a stir bar was added 6-(1H-tetrazol-1-yl)-3,4-dihydronaphthalen-2(1H)-one (30 mg, 0.14 mmol), Titanium (IV) isopropoxide (0.27 mL, 0.93 mmol), and sodium cyanoborohydride (29 mg, 0.46 mmol). The mixture was allowed to stir for 3 hours. LC showed formation of the desired product. The reaction was diluted with EtOAc, washed with brine, dried over sodium sulfate, filtered, concentrated and purified by mass-directed HPLC (0.1% TFA in water and acetonitrile). LC-MS (IE, m/z): 431 [M+1]+. (0.98 μM)

Sources & evidence

ORD record
ord-d1ed8ec5084b4fbd969146153483fe64
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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