Pyridine → HCID 10009345, compound

HRID 1062603Notes

Reaction equation

HRID 1062603 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-576a254ef2384c73b5a29d03fadaa4be
Source dataset
uspto-grants-2005_11
Patent number
US06962919B2

Reaction notes

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