2,6-Lutidine → HCID 89816146, compound

HRID 1487168Notes

Reaction equation

HRID 1487168 reaction equation
CC1C=CC(S(O[C:12]2[C:21]3[C:20](=[O:22])[N:19]([CH:23]4[CH2:25][CH2:24]4)[C:18](=[O:26])[N:17]([C:27]4[CH:32]=[CH:31][C:30]([I:33])=[CH:29][C:28]=4[F:34])[C:16]=3[N:15]([CH3:35])[C:14](=[O:36])[C:13]=2[CH3:37])(=O)=O)=CC=1.FC1C=C(I)C=CC=1NC1N(C)C(=O)C(C)=C2C=1C(=O)NC(=O)[N:52]2[C:59]1[CH:60]=[C:61]([CH2:65]CC(N)=O)[CH:62]=[CH:63][CH:64]=1.[N:73]1[C:78](C)=[CH:77][CH:76]=CC=1C.CC(N(C)C)=[O:83]>>[N:73]1([C:65]([C:61]2[CH:60]=[C:59]([NH:52][C:12]3[C:21]4[C:20](=[O:22])[N:19]([CH:23]5[CH2:25][CH2:24]5)[C:18](=[O:26])[N:17]([C:27]5[CH:32]=[CH:31][C:30]([I:33])=[CH:29][C:28]=5[F:34])[C:16]=4[N:15]([CH3:35])[C:14](=[O:36])[C:13]=3[CH3:37])[CH:64]=[CH:63][CH:62]=2)=[O:83])[CH2:76][CH2:77][CH2:78]1

Participants

5

Reactant 4

HCID 79372,6-LutidineHCID 31374DimethylacetamideHCID 597170443-Cyclopropyl-1-(2-fluoro-4-iodophenyl)-6,8-dimethyl-5-(((4-methylphenyl)sulfonyl)oxy)pyrido(2,3-d)pyrimidine-2,4,7(1H,3H,8H)-trioneHCID 71730181HCID 71730181, compound2×

Product 1

HCID 89816146HCID 89816146, compound

Conditions

Temperature
130 °C

Procedure

In a sealed tube 3-cyclopropyl-1-(2-fluoro-4-iodophenyl)-6,8-dimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydropyrido[2,3-d]pyrimidin-5-yl 4-methylbenzenesulfonate (4a) (0.5 g, 0.78 mmol), (3-aminophenyl)(azetidin-1-yl)methanone (intermediate 1) (0.27 g, 1.56 mmol) were taken to the mixture DMA (2 ml) and 2,6-lutidine (0.42 mg, 3.92 mmol) were added and the mixture was heated at 130° C. for 16 hr under nitrogen atmosphere. After completion of the reaction, the reaction mixture was poured into ice cold water, the separated solid was filtered off and washed with water and dried under vacuum. The crude solid was purified by column chromatography to yield the titled compound (0.11 g).

Workup

  1. additionwere added
  2. customAfter completion of the reaction
  3. additionthe reaction mixture was poured into ice cold water
  4. filtrationthe separated solid was filtered off
  5. washwashed with water
  6. customdried under vacuum
  7. customThe crude solid was purified by column chromatography

Sources & evidence

ORD record
ord-d03a80df23254b8fb80de182842deeb9
Source dataset
uspto-grants-2016_08
Patent number
US09428499B2

Reaction notes

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