Acetic Acid → HCID 46836601, compound

HRID 474217Notes

Reaction equation

[O:1]=[C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[N:20]=[CH:19][C:18]([O:21][CH2:22][CH:23]4[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]4)=[CH:17][N:16]=3)[CH:10]=2)[N:6]=[C:5]([C:29]2[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=2)[C:32]#[N:33])[CH:4]=[CH:3]1.C(O[BH-](O[C:47](=O)[CH3:48])OC(=O)C)(=O)C.[Na+].[C:51](O)(=O)C>CC(C)=O>[CH:47]([N:26]1[CH2:25][CH2:24][CH:23]([CH2:22][O:21][C:18]2[CH:17]=[N:16][C:15]([C:11]3[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=3)[CH2:8][N:7]3[C:2](=[O:1])[CH:3]=[CH:4][C:5]([C:29]4[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=4)[C:32]#[N:33])=[N:6]3)=[N:20][CH:19]=2)[CH2:28][CH2:27]1)([CH3:48])[CH3:51]

Participants

Conditions

Temperature: 40 °C

Procedure

150 mg (0.22 mmol) of 3-(6-oxo-1-{3-[5-(piperidin-4-ylmethoxy)pyrimidin-2-yl]benzyl}-1,6-dihydropyridazin-3-yl)benzonitrile is suspended in 5 ml of acetone, and 94 mg (0.45 mmol) of sodium triacetoxyborohydride are added. 200 μl of acetic acid are added to the reaction mixture, which is then stirred at 40° C. for 15 h. A further 94 mg (0.45 mmol) of sodium triacetoxyborohydride are subsequently added, and the mixture is stirred at 40° C. for 24 h. The reaction mixture is filtered, and the residue is washed with THF. The filtrate is stripped off to dryness and purified by means of preparative HPLC.

Workup

stirringthe mixture is stirred at 40° C. for 24 h
filtrationThe reaction mixture is filtered
washthe residue is washed with THF
custompurified by means of preparative HPLC

Sources & evidence

ORD record: ord-106bc06e392941ada8a8638886926c66
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637518B2

Reaction notes

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