Pyridine → HCID 10009345, compound

HRID 2227376Notes

Reaction equation

HRID 2227376 reaction equation
[CH:1]([O:4][C:5]([C:7]1[C:12](=[O:13])[N:11]2[C:14]([CH2:24][N:25]([CH3:33])[CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=3)[N:16]=[C:10]2[N:9]([CH2:34][C:35]2[C:40]([F:41])=[CH:39][CH:38]=[CH:37][C:36]=2[F:42])[CH:8]=1)=[O:6])([CH3:3])[CH3:2].N1C=CC=CC=1.[CH2:49]([N:51]=[C:52]=[O:53])[CH3:50]>C1COCC1>[CH:1]([O:4][C:5]([C:7]1[C:12](=[O:13])[N:11]2[C:14]([CH2:24][N:25]([CH3:33])[CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[C:15]([C:17]3[CH:18]=[CH:19][C:20]([NH:23][C:52]([NH:51][CH2:49][CH3:50])=[O:53])=[CH:21][CH:22]=3)[N:16]=[C:10]2[N:9]([CH2:34][C:35]2[C:40]([F:41])=[CH:39][CH:38]=[CH:37][C:36]=2[F:42])[CH:8]=1)=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8022Ethyl isocyanateHCID 22086866HCID 22086866, compound

Product 1

HCID 10009345HCID 10009345, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound obtained in Example 32 (1.37 g, 2.40 mmol) in THF (3 ml) is added pyridine (0.5 ml) and ethyl isocyanate (0.38 ml, 4.8 mmol). Then the mixture is stirred at room temperature overnight. The reaction mixture is concentrated under reduced pressure to give the residue, which triturated with isopropyl ether to afford a crystalline solid, which is recrystallized from chloroform-isopropyl ether to afford pale yellow crystals (1.20 g, 78%).

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customto give the residue, which
  3. customtriturated with isopropyl ether
  4. customto afford a crystalline solid, which
  5. customis recrystallized from chloroform-isopropyl ether

Sources & evidence

ORD record
ord-3d2100f367864e9da03131bfd42d7fc5
Source dataset
uspto-grants-2002_07
Patent number
US06413972B1

Reaction notes

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