Benzaldehyde → HCID 59191637, compound

HRID 1480011Notes

Reaction equation

[CH2:1]([C:8]1[N:9]=[N:10][C:11]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[C:12]([CH3:15])[C:13]=1[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.[CH:27](=O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C(O)(=O)C>[CH2:1]([C:8]1[N:9]=[N:10][C:11]([N:16]2[CH2:17][CH2:18][N:19]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:20][CH2:21]2)=[C:12]([CH3:15])[C:13]=1[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 3-benzyl-4,5-dimethyl-6-piperazin-1-yl-pyridazine (40 mg, 0.14 mmol)) in CH2Cl2 (1.6 mL) and THF (1.6 mL) at 25° C. is added benzaldehyde (23 mg, 0.21 mmol), acetic acid (2 drops) and sodium triacetoxyborohydride (90 mg, 0.43 mmol). After being stirred at 25° C. for 2 h, the mixture is diluted with CH2Cl2 (10 mL) and washed with saturated sodium bicarbonate (2 mL) and water (5 mL). The organic layer is concentrated and purified by HPLC (CH3CN/H2O: 22% 45% with 0.1% TFA) to give 3-benzyl-6-(4-benzyl-piperazin-1-yl)-4,5-dimethyl-pyridazine (20 mg, 37%).

Workup

washwashed with saturated sodium bicarbonate (2 mL) and water (5 mL)
concentrationThe organic layer is concentrated
custompurified by HPLC (CH3CN/H2O: 22% 45% with 0.1% TFA)

Sources & evidence

ORD record: ord-5f17493a55c5463d956badd66d87da0e
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409871B2

Reaction notes

Loading…