Pyridine → HCID 136336333, compound

HRID 2218259Notes

Reaction equation

HRID 2218259 reaction equation
[NH2:1][C:2]1[N:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[OH:21])[CH:12]=[C:11]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([NH2:28])[CH:23]=2)[C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].N1C=CC=CC=1.[O:35]=[C:36]1[O:40][CH:39]([C:41](Cl)=[O:42])[CH2:38][CH2:37]1>C1COCC1>[NH2:1][C:2]1[N:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[OH:21])[CH:12]=[C:11]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([NH:28][C:41]([CH:39]3[CH2:38][CH2:37][C:36](=[O:35])[O:40]3)=[O:42])[CH:23]=2)[C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5]

Participants

5

Reactant 3

HCID 1049PyridineHCID 108445405-Oxotetrahydro-2-furancarbonyl chlorideHCID 136336331HCID 136336331, compound2×

Product 1

HCID 136336333HCID 136336333, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cold (0° C.) solution of tert-butyl 2-amino-4-(3-aminophenyl)-6-(2-hydroxyphenyl)nicotinate (starting compound 6, 0.626 g, 1.659 mmol) in THF (7 mL) including pyridine (0.148 mL, 1.824 mmol) was added a solution of 5-oxotetrahydro-2-furancarbonyl chloride (0.271 g, 1.824 mmol) in THF (3 mL). After 1 hr., the mixture was allowed to warm to room temperature and the stirring was continued for 2 hrs. The mixture was partitioned between ethyl acetate and water. The separated organic phase was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica-gel (hexane:ethyl acetate, 1:4-1:19) to give tert-butyl 2-amino-6-(2-hydroxyphenyl)-4-(3-{[(5-oxotetrahydro-2-furanyl)carbonyl]amino}-phenyl)-nicotinate as a pale yellow foam (0.677 g, yield 83%).

Workup

  1. waitthe stirring was continued for 2 hrs
  2. customThe mixture was partitioned between ethyl acetate and water
  3. washThe separated organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica-gel (hexane:ethyl acetate, 1:4-1:19)

Sources & evidence

ORD record
ord-8e31b06f9d2b40e0b6c003276ae53f42
Source dataset
uspto-grants-2008_08
Patent number
US07410986B2

Reaction notes

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