Hydrochloric Acid → HCID 67416785, compound

HRID 474213Notes

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.Cl.[CH:38]1([CH:41]=O)[CH2:40][CH2:39]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1.[OH-].[Na+].C(O)(=O)C>[CH:38]1([CH2:41][N:26]2[CH2:25][CH2:24][CH:23]([CH2:22][O:21][C:18]3[CH:17]=[N:16][C:15]([C:11]4[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=4)[CH2:8][N:7]4[C:2](=[O:1])[CH:3]=[CH:4][C:5]([C:29]5[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=5)[C:32]#[N:33])=[N:6]4)=[N:20][CH:19]=3)[CH2:28][CH2:27]2)[CH2:40][CH2:39]1

Participants

Conditions

Temperature: 40 °C

Procedure

130 mg (0.185 mmol) of 3-(6-oxo-1-{3-[5-(piperidin-4-ylmethoxy)pyrimidin-2-yl]benzyl}-1,6-dihydropyridazin-3-yl)benzonitrile (liberated from the hydro-chloride by suspension in THF and extraction with 1N NaOH)), 28 μl (0.37 mmol) of cyclopropanecarboxaldehyde and 78 mg (0.37 mmo) of sodium triacetoxyborohydride are dissolved in 10 ml of THF, and 200 μl of acetic acid are added. The reaction mixture is stirred at 40° C. for 15 h. The reaction mixture is filtered and washed with THF. The filtrate is evaporated and purified by means of preparative HPLC.

Workup

filtrationThe reaction mixture is filtered
washwashed with THF
customThe filtrate is evaporated
custompurified by means of preparative HPLC

Sources & evidence

ORD record: ord-803d449b445248c59aec0e920f6225ef
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637518B2

Reaction notes

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