Pyridine → HCID 66894164, compound

HRID 252754Notes

Reaction equation

CS[C:3]([NH:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)=[CH:4][C:5]#[N:6].[NH2:14][CH2:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=O)=[CH:18][CH:17]=1.[N:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C[CH2:32][N:33](CC)CC>CN(C1C=CN=CC=1)C>[NH2:25][C:30]1[CH:29]=[CH:28][CH:27]=[CH:26][C:32]=1[NH:33][C:20](=[O:22])[C:19]1[CH:18]=[CH:17][C:16]([CH2:15][NH:14][C:3]([NH:7][C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[CH:4][C:5]#[N:6])=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 55 °C

Procedure

To a mixture of 3-methylsulfanyl-3-(pyridin-4-ylamino)-acrylonitrile (0.2 g, 1.0 mmol), 4-aminomethyl-benzoic acid (0.173 g, 1.14 mmol), DMAP (1 mg) and Et3N (0.14 ml, 1.0 mmol) was added dry pyridine (0.5 ml). The resulting stirring mixture was heated to 55° C. for 4.5 hrs., additional Et3N (0.14 ml) was added and mixture was heated from 75° C. to 90° C. over a period of −30 hrs. When the reaction was complete, pyridine was partially removed in vacuo and the crude was purified by column chromatography (gradient of EtOAc to 20% MeOH/EtOAc) to afford the desired product as an off-white solid (130 mg, 44%).

Workup

temperaturemixture was heated from 75° C. to 90° C. over a period of −30 hrs
custompyridine was partially removed in vacuo
customthe crude was purified by column chromatography (gradient of EtOAc to 20% MeOH/EtOAc)

Sources & evidence

ORD record: ord-c46ae51ce4c34c0ca830c0e3f00b8208
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07868204B2

Reaction notes

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