Water → HCID 22937003, compound

HRID 1433401Notes

Reaction equation

HRID 1433401 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:25]=[CH:24][C:23]([NH2:26])=[C:22]([F:27])[CH:21]=3)=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[C:28]#[N:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:30](Cl)(=[O:38])[O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.O.C1(C)C=CC=CC=1>CN(C)C=O.N1C=CC=CC=1>[C:28]([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[N:16]=[CH:15][CH:14]=[C:13]2[O:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:30](=[O:38])[O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[C:22]([F:27])[CH:21]=1)#[N:29]

Participants

7

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 15891Phenyl chloroformateHCID 22936431HCID 22936431, compound

Product 1

HCID 22937003HCID 22937003, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

The 7-benzyloxy-6-cyano-4-(3-fluoro-4-aminophenoxy)quinoline (9.45 g) synthesized in Production Example 8 was dissolved in dimethylformamide (70 ml) and pyridine (5.9 ml), and the mixture was cooled to 0° C. under a nitrogen atmosphere. After adding phenyl chlorocarbonate (3.4 ml), the mixture was stirred for 2 hours. Water was added to the reaction solution, and the precipitated crystals were filtered out and triturated in tetrahydrofuran and toluene to obtain 6.93 g of the title compound as light brown crystals (56% yield).

Workup

  1. filtrationthe precipitated crystals were filtered out
  2. customtriturated in tetrahydrofuran

Sources & evidence

ORD record
ord-b590ae0c8e7549a5879cb0004d60e462
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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