Potassium cyanate → HCID 70131165, compound

HRID 1934695Notes

Reaction equation

[O-:1][C:2]#[N:3].[K+].[C:5]([C:7]1[CH:8]=[CH:9][C:10]([NH:27][C@@H:28]2[CH2:32][CH2:31][NH:30][CH2:29]2)=[C:11]([CH:26]=1)[C:12]([NH:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=1)=[O:13])#[N:6]>O.C(O)(=O)C>[C:2]([N:30]1[CH2:31][CH2:32][C@@H:28]([NH:27][C:10]2[CH:9]=[CH:8][C:7]([C:5]#[N:6])=[CH:26][C:11]=2[C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=2)=[O:13])[CH2:29]1)(=[O:1])[NH2:3]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of potassium cyanate (53 mg) in water (1.5 mL) was added to a solution of (R)-5-cyano-N-(3,4-dimethoxybenzyl)-2-(3-pyrrolidinylamino)benzamide (100 mg) in acetic acid (1.5 mL). The mixture was stirred for 3 hours at 60° C. and then for 2 hours at 90° C. The reaction mixture was concentrated in vacuo and the residue was partitioned between chloroform and an aqueous saturated sodium bicarbonate solution. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The residue was purified by thin layer chromatography developed with 5% methanol in chloroform. The obtained product was triturated with diethyl ether to give (R)-2-(1-carbamoylpyrrolidin-3-ylamino)-5-cyano-N-(3,4-dimethoxybenzyl)benzamide (22 mg) as a powders.

Workup

waitfor 2 hours at 90° C
concentrationThe reaction mixture was concentrated in vacuo
customthe residue was partitioned between chloroform
dry with materialThe organic layer was dried over magnesium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by thin layer chromatography
customThe obtained product was triturated with diethyl ether

Sources & evidence

ORD record: ord-35067438c1ac45d2a739dbbd4ff3023a
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06384080B1

Reaction notes

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