Trifluoroacetic acid → HCID 118323997, compound

HRID 1778259Notes

Reaction equation

HRID 1778259 reaction equation
C([O:5][C:6]1[CH:15]=[C:14]([NH:16][CH:17]2[CH2:22][CH2:21][N:20]([S:23]([C:26]([F:29])([F:28])[F:27])(=[O:25])=[O:24])[CH2:19][CH2:18]2)[C:13]2[C:8](=[C:9]([NH:46][CH2:47][CH2:48][O:49][CH3:50])[CH:10]=[C:11]([C:30]([C:39]3[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=3)([C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=3)O)[CH:12]=2)[N:7]=1)(C)(C)C.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:38][C:35]1[CH:36]=[CH:37][C:32]([CH:30]([C:39]2[CH:40]=[CH:41][C:42]([Cl:45])=[CH:43][CH:44]=2)[C:11]2[CH:12]=[C:13]3[C:8](=[C:9]([NH:46][CH2:47][CH2:48][O:49][CH3:50])[CH:10]=2)[NH:7][C:6](=[O:5])[CH:15]=[C:14]3[NH:16][CH:17]2[CH2:22][CH2:21][N:20]([S:23]([C:26]([F:29])([F:27])[F:28])(=[O:25])=[O:24])[CH2:19][CH2:18]2)=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 118323969HCID 118323969, compound

Product 1

HCID 118323997HCID 118323997, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To solution of (2-(tert-butoxy)-8-((2-methoxyethyl)amino)-4-((1-((trifluoromethyl) sulfonyl)piperidin-4-yl)amino)quinolin-6-yl)bis(4-chlorophenyl)methanol (12 mg, 0.0159 mmol) and triethylsilane (0.0152 mL, 0.0953 mmol) in CH2Cl2 (1 mL) was added slowly TFA (0.03 mL, 0.392 mmol). The resulting mixture was stirred for 4 hr at room temperature. The reaction was diluted with CH2Cl2 and washed with Na2CO3 to make the aqueous layer basic. The organics were washed with water, dried over anhydrous Na2SO4 and concentrated. The resulting residue was triturated from Et2O/hexanes (1:3) to yield 6-(bis(4-chlorophenyl)methyl)-8-((2-methoxyethyl)amino)-4-((1-((trifluoromethyl)sulfonyl)piperidin-4-yl)amino)quinolin-2(1H)-one.

Workup

  1. washwashed with Na2CO3
  2. washThe organics were washed with water
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe resulting residue was triturated from Et2O/hexanes (1:3)

Sources & evidence

ORD record
ord-64b70c985a7e409cbbc51c62040e21e5
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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