Triethylamine → HCID 59436093, compound

HRID 1802472Notes

Reaction equation

HRID 1802472 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:26])=[C:7]([NH:9][C:10]2[C:19]3[CH:18]=[CH:17][NH:16][C:15](=[O:20])[C:14]=3[C:13]3[CH:21]=[C:22]([F:25])[CH:23]=[CH:24][C:12]=3[N:11]=2)[CH:8]=1.C(N(CC)CC)C.[F:34][C:35]([F:41])([F:40])[S:36](Cl)(=[O:38])=[O:37]>C1COCC1>[F:34][C:35]([F:41])([F:40])[S:36]([NH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:26])=[C:7]([NH:9][C:10]2[C:19]3[CH:18]=[CH:17][NH:16][C:15](=[O:20])[C:14]=3[C:13]3[CH:21]=[C:22]([F:25])[CH:23]=[CH:24][C:12]=3[N:11]=2)[CH:8]=1)(=[O:38])=[O:37]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79000Trifluoromethanesulfonyl chlorideHCID 59436027HCID 59436027, compound

Product 1

HCID 59436093HCID 59436093, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-{[5-(aminomethyl)-2-methylphenyl]amino}-9-fluorobenzo[c]-2,6-naphthyridin-1(2H)-one (35 mg, 0.10 mmol) in THF (1.0 mL) at 0° C. was added triethylamine (0.03 mL, 0.20 mmol) and trifluoromethanesufonyl chloride (0.01 mL, 0.11 mmol). The reaction was stirred for one hour and then quenched by the addition of citric acid. The mixture was extracted with EtOAc/water and the extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification by silica gel column chromatographpy (0-10% MeOH/CH2Cl2) afforded the title compound. 1H NMR (600 MHz, CD6SO) δ 12.21 (d, 1H), 9.92 (s, 1H), 9.45 (dd, 1H), 8.85 (s, 1H), 7.68 (m, 1H), 7.45 (m, 1H), 7.34-7.38 (m, 2H), 7.26 (d, 1H), 7.22 (d, 1H), 7.09 (d, 1H), 4.32 (s, 2H), 2.12 (s, 3H). LRMS (ESI) calc'd for C21H16F4N4O3 [M+H]+, 481.1; found 481.0.

Workup

  1. customquenched by the addition of citric acid
  2. extractionThe mixture was extracted with EtOAc/water
  3. washthe extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel column chromatographpy (0-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-2cc83fa9b9c14b0ea548276989bf71ce
Source dataset
uspto-grants-2013_01
Patent number
US08349865B2

Reaction notes

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