Hydrochloric Acid → HCID 178495295, compound

HRID 1793393Notes

Reaction equation

HRID 1793393 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][NH2:6].[F:7][C:8]1[C:17]2[NH:16][CH:15]=[C:14]3[C:18](=[O:30])[N:19]([C:21]4[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=4)[C:24](Cl)=[O:25])[N:20]=[C:13]3[C:12]=2[CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C.Cl>O1CCCC1>[F:7][C:8]1[C:17]2[NH:16][CH:15]=[C:14]3[C:18](=[O:30])[N:19]([C:21]4[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=4)[C:24]([NH:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])=[O:25])[N:20]=[C:13]3[C:12]=2[CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 16723-MethoxypropylamineHCID 8471TriethylamineHCID 178521108HCID 178521108, compound2×

Product 1

HCID 178495295HCID 178495295, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Methoxypropylamine (0.026 g, 0.29 mmol) was added to a stirred solution of 3-(6-fluoro-3-oxo-3,5-dihydro-pyrazolo[4,3-c]quinolin-2-yl)-benzoyl chloride (intermediate 4) (26 mg 0.29 mmol) in tetrahydrofuran (2 ml) and the mixture stirred at room temperature for 15 min. Triethylamine (0.2 ml, 1.4 mmol) was then added and the resulting mixture stirred overnight. 1M Hydrochloric acid (3–4 ml) was added dropwise to precipitate a yellow solid which was filtered and dried under suction to give the amide (79 mg, 0.20 mmol) as a yellow solid, LCMS m/z 395.25 [M+H]+ @ RT 1.04 min; δH(400 MHz, (CD3)2SO) 8.59 (1H, m), 8.57 (1H, s), 8.39 (1H, app d J 9.3 Hz), 8.08 (1H, app d J 7.3 Hz), 7.66–7.53 (5H, m), 3.37–3.33 (4H, m), 3.27 (3H, s), 1.83–1.77 (2H, m).

Workup

  1. stirringthe resulting mixture stirred overnight
  2. customto precipitate a yellow solid which
  3. filtrationwas filtered
  4. customdried under suction

Sources & evidence

ORD record
ord-17c5c40e4c584119be22329d4d1bff41
Source dataset
uspto-grants-2006_07
Patent number
US07081456B2

Reaction notes

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