Water → HCID 10162773, compound

HRID 387706Notes

Reaction equation

HRID 387706 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][O:16][CH3:17])[N:9]=[CH:8][CH:7]=[C:6]2[O:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26](=O)[O:27]C2C=CC=CC=2)=[C:21]([F:35])[CH:20]=1)#[N:2].[NH2:36][C:37]1[S:38][CH:39]=[CH:40][N:41]=1.C(N(CC)CC)C.O>CN(C)C=O>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][O:16][CH3:17])[N:9]=[CH:8][CH:7]=[C:6]2[O:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([NH:36][C:37]2[S:38][CH:39]=[CH:40][N:41]=2)=[O:27])=[C:21]([F:35])[CH:20]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 21552-AminothiazoleHCID 8471TriethylamineHCID 22936698HCID 22936698, compound

Product 1

HCID 10162773HCID 10162773, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Phenyl N-(4-(6-cyano-7-(2-methoxyethoxy)-4-quinolyl)oxy-2-fluorophenyl)carbamate (200 mg) and 2-aminothiazole (85 mg) were dissolved in 1 ml of dimethylformamide, and then 0.12 ml of triethylamine was added thereto 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 110 mg of the title compound as light brown crystals (57% 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-1b54bc15a476409d87b7f3e4be5373aa
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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