5-amino-3-chloro-1-(4-methoxy-benzyl)-1H-pyridin-2-one → Ethyl 4-((5-chloro-1-(4-methoxybenzyl)-6-oxo-1,6-dihydropyridin-3-ylamino)(4-cyano-3-fluorophenyl)methyl)-1-(2-(dimethylamino)-4-methoxypyrimidin-5-yl)-5-isopropyl-1H-pyrazole-3-carboxylate

HRID 869082Notes

Reaction equation

HRID 869082 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9](O)[C:10]2[C:11]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[N:12][N:13]([C:18]3[C:19]([O:27][CH3:28])=[N:20][C:21]([N:24]([CH3:26])[CH3:25])=[N:22][CH:23]=3)[C:14]=2[CH:15]([CH3:17])[CH3:16])=[CH:5][C:4]=1[F:35])#[N:2].[NH2:36][C:37]1[CH:38]=[C:39]([Cl:53])[C:40](=[O:52])[N:41]([CH2:43][C:44]2[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[CH:46][CH:45]=2)[CH:42]=1>>[Cl:53][C:39]1[C:40](=[O:52])[N:41]([CH2:43][C:44]2[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[CH:46][CH:45]=2)[CH:42]=[C:37]([NH:36][CH:9]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[C:4]([F:35])[CH:5]=2)[C:10]2[C:11]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[N:12][N:13]([C:18]3[C:19]([O:27][CH3:28])=[N:20][C:21]([N:24]([CH3:26])[CH3:25])=[N:22][CH:23]=3)[C:14]=2[CH:15]([CH3:17])[CH3:16])[CH:38]=1

Participants

3

Reactant 2

HCID 867031245-amino-3-chloro-1-(4-methoxy-benzyl)-1H-pyridin-2-oneHCID 89601400ethyl 4-((4-cyano-3-fluorophenyl)(hydroxy)methyl)-1-(2-(dimethylamino)-4-methoxypyrimidin-5-yl)-5-isopropyl-1H-pyrazole-3-carboxylate2×

Product 1

HCID 89611255Ethyl 4-((5-chloro-1-(4-methoxybenzyl)-6-oxo-1,6-dihydropyridin-3-ylamino)(4-cyano-3-fluorophenyl)methyl)-1-(2-(dimethylamino)-4-methoxypyrimidin-5-yl)-5-isopropyl-1H-pyrazole-3-carboxylate

Procedure

The title compound was prepared in analogy to the procedure described in step 184.2 but using ethyl 4-((4-cyano-3-fluorophenyl)(hydroxy)methyl)-1-(2-(dimethylamino)-4-methoxypyrimidin-5-yl)-5-isopropyl-1H-pyrazole-3-carboxylate (intermediate 191.3) and 5-amino-3-chloro-1-(4-methoxy-benzyl)-1H-pyridin-2-one (product from step 155.4). After the extraction, the crude product was purified by chromatography (Silicagel, Hexane/EtOAc 50:50 to 20:80). Pure fractions were collected and evaporated to dryness to afford a brown solid.

Workup

  1. extractionAfter the extraction
  2. customthe crude product was purified by chromatography (Silicagel, Hexane/EtOAc 50:50 to 20:80)
  3. customPure fractions were collected
  4. customevaporated to dryness
  5. customto afford a brown solid

Sources & evidence

ORD record
ord-c734d6f6bf544af3a8bb95c2a69c0001
Source dataset
uspto-grants-2015_03
Patent number
US08969341B2

Reaction notes

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