Water → HCID 66713183, compound

HRID 870549Notes

Reaction equation

N[CH2:2][C@H:3]1[CH2:7][NH:6][C:5](=[O:8])[CH2:4]1.Cl[C:10]1[N:19]=[C:18]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH:27]([CH3:29])[CH3:28])=[C:22]([F:30])[CH:21]=2)[CH:17]=[C:16]2[C:11]=1[CH:12]=[CH:13][CH:14]=[N:15]2.[OH2:31]>CC(N(C)C)=O>[F:30][C:22]1[CH:21]=[C:20]([C:18]2[CH:17]=[C:16]3[C:11]([CH:12]=[CH:13][CH:14]=[N:15]3)=[C:10]([O:31][CH2:2][C@H:3]3[CH2:7][NH:6][C:5](=[O:8])[CH2:4]3)[N:19]=2)[CH:25]=[CH:24][C:23]=1[O:26][CH:27]([CH3:29])[CH3:28]

Participants

Conditions

Temperature: 100 °C

Procedure

224 mg (R)-4-Hydroxymethyl-pyrrolidine-2-one (2.2) was placed in 1.5 mL of dimethylacetamide at ambient temperature under nitrogen. The reaction was stirred for 10 min before 5-chloro-7-(3-fluoro-4-isopropoxy-phenyl)-[1,6]naphthyridine (6.41) as a solution in 3 mL dimethylacetamide was introduced. The reaction was heated to 100° C. for 3 h and then cooled to ambient temperature. Water was added and the mixture was extracted with ethyl acetate (×3). The combined organic fractions were dried over sodium sulfate, filtered and the filtrate was concentrated under reduced pressure. Purification by silica gel chromatography (ethyl acetate/methanol: 100:0 to 90:10) gave the title compound.

Workup

additionwas introduced
temperaturecooled to ambient temperature
extractionthe mixture was extracted with ethyl acetate (×3)
dry with materialThe combined organic fractions were dried over sodium sulfate
filtrationfiltered
concentrationthe filtrate was concentrated under reduced pressure
customPurification by silica gel chromatography (ethyl acetate/methanol: 100:0 to 90:10)

Sources & evidence

ORD record: ord-c59867d1bc61475ba0b08ce5065a82be
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969568B2

Reaction notes

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