Potassium Carbonate → HCID 16065530, compound

HRID 2425520Notes

Reaction equation

HRID 2425520 reaction equation
Br[CH2:2][C:3]1[C:4]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:5][C:6]2[C:11]([C:12]=1[C:13]([NH:15][C@H:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:17][CH3:18])=[O:14])=[CH:10][CH:9]=[CH:8][CH:7]=2.C([O-])([O-])=O.[K+].[K+].[SH:37][C:38]1[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=1>CC#N>[C:25]1([C:4]2[C:3]([CH2:2][S:37][C:38]3[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=3)=[C:12]([C:13]([NH:15][C@H:16]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:17][CH3:18])=[O:14])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 16064396HCID 16064396, compoundHCID 178418431pyridine-4-thiol

Product 1

HCID 16065530HCID 16065530, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-(bromomethyl)-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-4-carboxamide (8) (150 mg, 0.33 mmol) was dissolved in CH3CN (2 mL) under N2 and to this, with stirring, was added K2CO3 (140 mg, 0.99 mmol), then 4-mercaptopyridine (40 mg, 0.36 mmol). The suspension was allowed to stir overnight; concentrated; diluted with EtOAc; washed with 0.5 N NaOH, then H2O; dried over Na2SO4; filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (EtOAc/CH2Cl2) to afford the desired product as oil (120 mg, 74% yield). 1H NMR (300 MHz, CDCl3, 52° C.) δ 8.30 (s, 2H), 8.14 (d, J=8.4 Hz, 1H), 7.80 (d, J=7.2 Hz, 1H), 7.76-7.69 (m, 1H), 7.62-7.49 (m, 3H), 7.43-7.37 (m, 3H), 7.35-7.28 (m, 2H), 7.25-7.19 (m, 3H), 6.80 (d, J=4.4 Hz, 2H), 6.37 (d, J=7.9 Hz, 1H), 5.21 (q, J=7.6 Hz, 1H), 4.36-4.23 (m, 2H), 2.08-1.82 (m, 2H), 0.95 (t, J=7.4 Hz, 3H); HRMS m/z 490.1931, calcd 490.1953.

Workup

  1. stirringto stir overnight
  2. concentrationconcentrated
  3. additiondiluted with EtOAc
  4. washwashed with 0.5 N NaOH
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-ef5ace98dbf74facac2b1a86e0e2c194
Source dataset
uspto-grants-2011_06
Patent number
US07964733B2

Reaction notes

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