Diisopropylethylamine → 8-Methyl-7-{[4-({4-[(trifluoromethyl)oxy]phenyl}sulfonyl)-1-piperazinyl]carbonyl}quinoline

HRID 2365449Notes

Reaction equation

HRID 2365449 reaction equation
[CH3:1][C:2]1[C:3]([C:12]([OH:14])=O)=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:39][C:40]([F:58])([F:57])[O:41][C:42]1[CH:47]=[CH:46][C:45]([S:48]([N:51]2[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]2)(=[O:50])=[O:49])=[CH:44][CH:43]=1.CCN(C(C)C)C(C)C>CN(C)C=O>[CH3:1][C:2]1[C:3]([C:12]([N:54]2[CH2:53][CH2:52][N:51]([S:48]([C:45]3[CH:46]=[CH:47][C:42]([O:41][C:40]([F:57])([F:58])[F:39])=[CH:43][CH:44]=3)(=[O:49])=[O:50])[CH2:56][CH2:55]2)=[O:14])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 20794021-[4-(Trifluoromethoxy)benzenesulfonyl]piperazine2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 597495658-Methylquinoline-7-carboxylic acid2×

Product 1

HCID 673234128-Methyl-7-{[4-({4-[(trifluoromethyl)oxy]phenyl}sulfonyl)-1-piperazinyl]carbonyl}quinolineYield 49.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the solution of 8-methyl-7-quinolinecarboxylic acid (may be prepared as described in Intermediate 2; 90 mg, 0.483 mmol) in N,N-Dimethylformamide (DMF) (2 ml), HATU (193 mg, 0.508 mmol) was added at room temperature. The reaction was stirred for 20 min and then 1-({4-[(trifluoromethyl)oxy]phenyl}sulfonyl)piperazine (may be prepared as described in Intermediate 11; 150 mg, 0.483 mmol) was added followed by DIPEA (0.211 ml, 1.209 mmol) and the reaction mixture was stirred for 3 hours. The reaction mixture was poured into the separating funnel and partitioned between ethyl acetate (25 ml) and sodium hydroxide (15 ml). The organic phase was washed with sodium hydroxide (2×10 ml), water (2×10 ml) and brine (10 mL) before it was dried using phase separator and the solvent was removed under vacuum. The crude product was purified by MDAP to give the title compound as a white solid (115 mg).

Workup

  1. stirringthe reaction mixture was stirred for 3 hours
  2. additionThe reaction mixture was poured into the separating funnel
  3. custompartitioned between ethyl acetate (25 ml) and sodium hydroxide (15 ml)
  4. washThe organic phase was washed with sodium hydroxide (2×10 ml), water (2×10 ml) and brine (10 mL) before it
  5. customwas dried
  6. customthe solvent was removed under vacuum
  7. customThe crude product was purified by MDAP

Sources & evidence

ORD record
ord-abdbf5896023457fa2d80a1e3c818abb
Source dataset
uspto-grants-2014_04
Patent number
US08697703B2

Reaction notes

Loading…