Ethyl trifluoroacetate → HCID 136335677, compound

HRID 2377862Notes

Reaction equation

HRID 2377862 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[F:12])[NH:5][C:4](=[O:13])[C:3]=1[C:14]1[NH:18][C:17]2[CH:19]=[C:20]([N:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[CH:21]=[CH:22][C:16]=2[N:15]=1.[F:29][C:30]([F:37])([F:36])[C:31](OCC)=[O:32]>CN(C)C(=O)C>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[F:12])[NH:5][C:4](=[O:13])[C:3]=1[C:14]1[NH:18][C:17]2[CH:19]=[C:20]([N:23]3[CH2:28][CH2:27][N:26]([C:31](=[O:32])[C:30]([F:37])([F:36])[F:29])[CH2:25][CH2:24]3)[CH:21]=[CH:22][C:16]=2[N:15]=1

Participants

4

Reactant 2

HCID 9794Ethyl trifluoroacetateHCID 135543684N-Desmethyl Dovitinib

Product 1

HCID 136335677HCID 136335677, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
130 °C

Procedure

4-Amino-5-fluoro-3-(6-piperazin-1-yl-1H-benzoimidazol-2-yl)-1H-quinolin-2-one was taken up in ethyl trifluoroacetate and N,N-dimethylacetamide (DMA). The resulting solution was heated at 130° C. in a sealed tube for 30 minutes. The reaction was cooled to room temperature and quenched by addition of saturated aqueous sodium bicarbonate followed by pouring the mixture into water. The resulting solid was collected by filtration and washed with diethyl ether to afford 4-amino-5-fluoro-3-{6-[4-(2,2,2-trifluoro-acetyl)-piperazin-1-yl]-1H-benzoimidazol-2-yl}-1H-quinolin-2-one (Rt 2.63 minutes, MH+=457.1), which was immediately taken up in THF. Borane-THF complex (3.3 equivalents) was added and the reaction was stirred at room temperature overnight. After quenching the excess borane with water, the mixture was extracted into ethyl acetate, dried over magnesium sulfate, filtered and concentrated to a brown solid which was purified by reverse phase HPLC to yield the desired compound. MH+=461.1.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customquenched by addition of saturated aqueous sodium bicarbonate
  3. additionby pouring the mixture into water
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with diethyl ether

Sources & evidence

ORD record
ord-842e34216cfd4e2aa5215e748fe7769a
Source dataset
uspto-grants-2008_12
Patent number
US07470709B2

Reaction notes

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