Citric Acid → 2-({[3-Chloro-1-(2,6-difluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridin-4-yl]oxy}methyl)-5-fluorobenzonitrile

HRID 201301Notes

Reaction equation

HRID 201301 reaction equation
[Br:1][CH2:2][c:3]1[c:4]([C:5]#[N:6])[cH:7][c:8]([F:11])[cH:9][cH:10]1.[CH3:67][N:68]([CH3:69])[C:70](=[O:71])[CH3:72].[Cl:12][c:13]1[c:14](=[O:29])[n:15](-[c:21]2[c:22]([F:28])[cH:23][cH:24][cH:25][c:26]2[F:27])[c:16]([CH3:20])[cH:17][c:18]1[OH:19].[K+:30].[K+:31].[O-:32][C:33]([O-:34])=[O:35].[O:36]1[CH2:37][CH2:38][O:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][O:45][CH2:46][CH2:47][O:48][CH2:49][CH2:50][O:51][CH2:52][CH2:53]1.[OH:54][C:55]([CH2:56][C:57]([C:58](=[O:59])[OH:60])([CH2:61][C:62](=[O:63])[OH:64])[OH:65])=[O:66]>>[CH2:2]([c:3]1[c:4]([C:5]#[N:6])[cH:7][c:8]([F:11])[cH:9][cH:10]1)[O:19][c:18]1[c:13]([Cl:12])[c:14](=[O:29])[n:15](-[c:21]2[c:22]([F:28])[cH:23][cH:24][cH:25][c:26]2[F:27])[c:16]([CH3:20])[cH:17]1

Participants

8

Reactant 7

HCID 311Citric AcidHCID 813Potassium Cation2×HCID 19660Carbonate IonHCID 2855718-Crown-6HCID 31374DimethylacetamideHCID 220157702-(Bromomethyl)-5-fluorobenzonitrileHCID 547242093-chloro-1-(2,6-difluorophenyl)-4-hydroxy-6-methylpyridin-2(1H)-one

Product 1

HCID 220500172-({[3-Chloro-1-(2,6-difluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridin-4-yl]oxy}methyl)-5-fluorobenzonitrile

Sources & evidence

ORD record
ord-4a5931c519df4202a9469211924915e3
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (6/10)

Reaction notes

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