Benzyl Alcohol → N-{4-[2-Amino-6-(benzyloxy)-3,5-dicyano-4-pyridinyl]phenyl}acetamide

HRID 2264523Notes

Reaction equation

[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[CH:12][CH:11]=2)[C:5]([C:20]#[N:21])=[C:4](SC2C=CC=CC=2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:35]([OH:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[CH:12][CH:11]=2)[C:5]([C:20]#[N:21])=[C:4]([O:42][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[N:3]=1

Participants

Reactant 3

HCID 244Benzyl Alcohol

HCID 11430Potassium Carbonate

HCID 12016387N-{4-[2-Amino-3,5-dicyano-6-(phenylsulphanyl)-4-pyridinyl]phenyl}acetamide

Product 1

HCID 10221564N-{4-[2-Amino-6-(benzyloxy)-3,5-dicyano-4-pyridinyl]phenyl}acetamide

Conditions

Temperature: 100 °C

Procedure

58 mg (0.15 mmol) of N-{4-[2-amino-3,5-dicyano-6-(phenylsulfanyl)-4-pyridinyl]phenyl}acetamide [prepared analogously to Kambe et al., Synthesis, 531-533 (1981)] are, together with 41 mg (0.3 mmol) of potassium carbonate, dissolved/suspended in 1.88 g (=1.8 ml, 17.4 mmol) of benzyl alcohol, and the mixture is stirred at 100° C. for 3.5 h. The benzyl alcohol is evaporated under reduced pressure and the evaporation residue is purified by preparative HPLC on reversed-phase silica gel (gradient: water/acetonitrile 90:1010:90 in 38 minutes).

Workup

customThe benzyl alcohol is evaporated under reduced pressure
customthe evaporation residue is purified by preparative HPLC on reversed-phase silica gel (gradient: water/acetonitrile 90:1010:90 in 38 minutes)

Sources & evidence

ORD record: ord-6a6345a0e9c445b8ae3a4ec1262644f8
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855219B2

Reaction notes

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