Benzyl Alcohol → HCID 10109707, compound

HRID 2264525Notes

Reaction equation

Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]([C:16]#[N:17])=[C:4]([NH:18][CH2:19][CH2:20][OH:21])[N:3]=1.CC(C)([O-])C.[K+].[CH2:28]([OH:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>>[CH2:28]([O:35][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]([C:16]#[N:17])=[C:4]([NH:18][CH2:19][CH2:20][OH:21])[N:3]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

Reactant 3

HCID 244Benzyl Alcohol

HCID 179760112-Chloro-4-phenyl-6-(2-hydroxyethylamino)-3,5-pyridinedicarbonitrile

HCID 23665647Potassium tert-butoxide

Product 1

HCID 10109707HCID 10109707, compound

Conditions

Temperature: 40 °C

Procedure

58 mg (0.2 mmol) of 2-chloro-4-phenyl-6-(2-hydroxyethylamino)-3,5-pyridinedicarbonitrile (example 17, step 1) are, together with 27 mg (0.24 mmol) of potassium tert-butoxide, dissolved in 0.96 g (=1 ml, 8.9 mmol) of benzyl alcohol, and the mixture is stirred at 40° C. for about 16 h. The reaction mixture is purified by preparative HPLC on reversed-phase silica gel (gradient: water+0.1% formic acid/acetonitrile 90:105:95 in 35 minutes).

Workup

customThe reaction mixture is purified by preparative HPLC on reversed-phase silica gel (gradient: water+0.1% formic acid/acetonitrile 90:105:95 in 35 minutes)

Sources & evidence

ORD record: ord-1f44fdf5372b4df59e58f6e1055a874a
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855219B2

Reaction notes

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