Triethylamine → HCID 90449237, compound

HRID 589381Notes

Reaction equation

HRID 589381 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([F:16])[CH:14]=3)[C:9]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:8]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:32]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=[CH:34][C:33]=1[C:42](Cl)=[O:43].C(=O)(O)[O-].[Na+]>ClCCl>[CH:32]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=[CH:34][C:33]=1[C:42]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([F:16])[CH:14]=3)[C:9]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:8]2)=[CH:23][CH:24]=1)=[O:43]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 752462-Naphthoyl chlorideHCID 516892Sodium BicarbonateHCID 89590287HCID 89590287, compound

Product 1

HCID 90449237HCID 90449237, compoundYield 42.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The crude ethyl 2-[1-(4-aminobenzyl)-6-fluoro-1H-indazol-3-yl]acetate (about 1.0 mmol) obtained in the last step and triethylamine (0.5 mL) were dissolved in dichloromethane (15 mL). In an ice bath, dichloromethane solution (10 mL) of 2-naphthoyl chloride (191 mg, 1.0 mmol) was added dropwise slowly. Upon completion of the dropwise addition, it was reacted at room temperature for 16 hours. An aqueous solution of sodium bicarbonate was added to quench, and extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduce pressure, chromatographed on a silica gel column (petroleum ether:ethyl acetate=2:1) to obtain a white solid 205 mg, at a total yield over two steps of reactions of 42.6%.

Workup

  1. additionUpon completion of the dropwise addition, it
  2. customwas reacted at room temperature for 16 hours
  3. customto quench
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customchromatographed on a silica gel column (petroleum ether:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-a62bbce8d6904e87a18ba20331aeadf3
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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