Water → HCID 22936427, compound

HRID 853272Notes

Reaction equation

HRID 853272 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[N:9]=[CH:8][CH:7]=[C:6]2[O:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29](=O)[O:30]C2C=CC=CC=2)=[C:24]([F:38])[CH:23]=1)#[N:2].[NH2:39][C:40]1[S:41][CH:42]=[CH:43][N:44]=1.C(N(C(C)C)CC)(C)C.O>CN(C)C=O>[CH2:14]([O:13][C:12]1[CH:11]=[C:10]2[C:5]([C:6]([O:21][C:22]3[CH:27]=[CH:26][C:25]([NH:28][C:29]([NH:39][C:40]4[S:41][CH:42]=[CH:43][N:44]=4)=[O:30])=[C:24]([F:38])[CH:23]=3)=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[C:1]#[N:2])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 21552-AminothiazoleHCID 81531DiisopropylethylamineHCID 22937003HCID 22937003, compound

Product 1

HCID 22936427HCID 22936427, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Phenyl N-(4-(6-cyano-7-benzyloxy-4-quinolyl)oxy-2-fluorophenyl)carbamate (6.93 g) and 2-aminothiazole (2.75 g) were dissolved in dimethylformamide (70 ml), and then diisopropylethylamine (4.8 ml) was added and the mixture was heated and stirred at 90° C. for 2 hours. After cooling, water was added and the precipitated solid was filtered out and washed with ethyl acetate to obtain 5.53 g of the title compound as light brown crystals (79% yield).

Workup

  1. temperaturethe mixture was heated
  2. temperatureAfter cooling
  3. filtrationthe precipitated solid was filtered out
  4. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-bc3ee29dc9ab40f8ba37fa7db90b958f
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

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