Triethylamine → HCID 178527444, compound

HRID 1778231Notes

Reaction equation

HRID 1778231 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]=[C:14]([OH:19])[CH:13]=[C:12]3[NH:20][CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[CH:4][CH:3]=1.[N:34]1([S:39](Cl)(=[O:41])=[O:40])[CH2:38][CH2:37][CH2:36][CH2:35]1.C(N(CC)CC)C>ClCCl>[Cl:33][C:30]1[CH:29]=[CH:28][C:27]([CH:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]=[C:14]([OH:19])[CH:13]=[C:12]3[NH:20][CH:21]2[CH2:22][CH2:23][N:24]([S:39]([N:34]3[CH2:38][CH2:37][CH2:36][CH2:35]3)(=[O:41])=[O:40])[CH2:25][CH2:26]2)=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 64839021-Pyrrolidinesulfonyl chlorideHCID 178516447HCID 178516447, compound

Product 1

HCID 178527444HCID 178527444, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 8-mL round-bottom flask, was placed 6-[bis(4-chlorophenyl)methyl]-4-[(piperidin-4-yl)amino]quinolin-2-ol (70 mg, 0.15 mmol, 1.00 equip), dichloromethane (3 mL), pyrrolidine-1-sulfonyl chloride (37.2 mg, 0.22 mmol, 1.50 equip), and triethylamine (44.6 mg, 0.44 mmol, 3.01 equip). The resulting solution was stirred for 2 h at room temperature. The reaction was then quenched by the addition of water (100 mL). The resulting solution was extracted with ethyl acetate (3×50 mL) and the organic layers combined and dried over anhydrous sodium sulfate. The solids were filtered out. The filtrate was concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol (20:1). The resulting residue was recrystallized from ethyl acetate:petroleum ether in the ratio of 1:10 to yield 6-[bis(4-chlorophenyl)methyl]-4-[[1-(pyrrolidine-1-sulfonyl)piperidin-4-yl]amino]quinolin-2-ol as an off-white solid.

Workup

  1. customInto a 8-mL round-bottom flask, was placed
  2. customThe reaction was then quenched by the addition of water (100 mL)
  3. extractionThe resulting solution was extracted with ethyl acetate (3×50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe solids were filtered out
  6. concentrationThe filtrate was concentrated under vacuum
  7. customThe resulting residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-e843239b71584100a372d2547a7b64e7
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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