Pyridine → HCID 44180626, compound

HRID 1042029Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[O:13][C:14]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[CH:15][C:16](=[O:17])[C:11]=3[S:10][CH:9]=2)=[CH:4][CH:3]=1.[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl.[C:31](Cl)(=[O:38])C1C=CN=CC=1>ClCCl>[O:21]1[CH2:22][CH2:23][N:18]([C:14]2[O:13][C:12]3[C:8]([C:5]4[CH:6]=[CH:7][C:2]([NH:1][C:31](=[O:38])[C:26]5[CH:27]=[CH:28][CH:29]=[N:24][CH:25]=5)=[CH:3][CH:4]=4)=[CH:9][S:10][C:11]=3[C:16](=[O:17])[CH:15]=2)[CH2:19][CH2:20]1

Participants

Conditions

Temperature: 0 °C

Procedure

A 40 mL vial was charged with a magnetic stirring bar, 3-(4-aminophenyl)-5-morpholino-7H-thieno[3,2-b]pyran-7-one (56) (200 mg, 609 μmol) and pyridine (5 mL). The mixture was magnetically stirred and cooled to 0° C. in an ice bath. Isonicotinoyl chloride hydrochloric acid (669 μmol) was added and the reaction was stirred at room temperature for 30 minutes. The reaction was diluted with dichloromethane (15 mL) and washed three times with saturated aqueous sodium bicarbonate solution (15 mL). The dichloromethane layer was dried over magnesium sulfate, filtered, and concentrated in vacuo to give N-(4-(5-morpholino-7-oxo-7H-thieno[3,2-b]pyran-3-yl)phenyl)nicotinamide (30) (94 mg, 217 μmol) as a yellow solid.

Workup

additionA 40 mL vial was charged with a magnetic stirring bar
stirringthe reaction was stirred at room temperature for 30 minutes
washwashed three times with saturated aqueous sodium bicarbonate solution (15 mL)
dry with materialThe dichloromethane layer was dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-60388082878347b28aac8117dc889eb1
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557807B2

Reaction notes

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