Phenylacetyl chloride → HCID 11397684, compound

HRID 705607Notes

Reaction equation

HRID 705607 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2C(=C[C:12]=1OC)N=[C:8]([O:15][C:16]1[C:25]([F:26])=[CH:24][C:19]3[N:20]=[C:21]([NH2:23])[S:22][C:18]=3[CH:17]=1)[CH:7]=[CH:6]2.CC[N:29]([CH2:32][CH3:33])CC.[C:34]1([CH2:40][C:41](Cl)=[O:42])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C1C[O:47][CH2:46]C1>C(C#N)(C)=O>[CH3:1][O:2][C:3]1[CH:12]=[C:7]2[C:6](=[CH:5][C:4]=1[O:47][CH3:46])[N:29]=[CH:32][CH:33]=[C:8]2[O:15][C:16]1[C:25]([F:26])=[CH:24][C:19]2[N:20]=[C:21]([NH:23][C:41](=[O:42])[CH2:40][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[S:22][C:18]=2[CH:17]=1

Participants

6

Reactant 4

HCID 7679Phenylacetyl chloride2×HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 86611277HCID 86611277, compound

Product 1

HCID 11397684HCID 11397684, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 694302-OxopropiononitrileSolvent

Procedure

6-(6,7-dimethoxy-quinolinyloxy)-5-fluoro-benzothiazol-2-ylamine (95 mg, 0.25 mmol), Et3N (0.10 ml, 0.72 mmol), phenylacetyl chloride (0.044 ml, 0.33 mmol), and THF (11.0 ml) were combined and stirred at room temperature for 1 hr. Additional phenylacetyl chloride (0.044 ml, 0.33 mmol) was added and the mixture heated to reflux for 1-2 hrs. After cooling to room temperature, the reaction mixture was diluted with 1:1 AcCN:H2O (11.0 ml) and the resulting solids filtered, washed with 1:1 AcCN:H2O and dried under high vacuum to give N-[6-(6,7-dimethoxy-quinolin-4-yloxy)-5-fluoro-benzothiazol-2-yl]-2-phenyl-acetamide (72 mgs, 59%). 1H-NMR (400 MHz, DMSO): 12.80 (s, 1H), 8.54 (d, 1H), 8.18 (d, 1H), 7.91 (d, 1H), 7.60 (s, 1H), 7.45 (s, 1H), 7.34 (m, 4H), 7.28 (m, 1H), 6.60 (d, 1H), 3.98 (s, 3H), 3.96 (s, 3H), 3.86 (s, 2H). LC/MS Calcd for [M+H]+ 490.1. found 490.0.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 1-2 hrs
  3. temperatureAfter cooling to room temperature
  4. filtrationH2O (11.0 ml) and the resulting solids filtered
  5. washwashed with 1:1 AcCN
  6. dry with materialH2O and dried under high vacuum

Sources & evidence

ORD record
ord-12821a2027f34d9a9ae7d36b5485e8a3
Source dataset
uspto-grants-2015_11
Patent number
US09174947B2

Reaction notes

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