Ammonium Chloride → HCID 68154122, compound

HRID 341104Notes

Reaction equation

HRID 341104 reaction equation
[NH2:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:10]3=[N:17][N:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH3:27])[C:19](=[O:20])[C:9]3=[CH:8]2)=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[CH3:35][S:36](Cl)(=[O:38])=[O:37].[Cl-].[NH4+]>ClCCl>[CH3:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[N:18]1[C:19](=[O:20])[C:9]2=[CH:8][N:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([NH:1][S:36]([CH3:35])(=[O:38])=[O:37])=[CH:29][CH:28]=3)[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:10]2=[N:17]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 69935372HCID 69935372, compound

Product 1

HCID 68154122HCID 68154122, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

5-(4-Aminobenzyl)-2-(2-methylphenyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one (Example 756, 35 mg, 0.092 mmol) and sodium bicarbonate (23 mg, 0.28 mmol, 3 equiv) were combined in dichloromethane (2 mL) and cooled to 0° C. The mixture was treated with methanesulfonyl chloride (0.071 mL, 0.92 mmol, 10 equiv), stirred for 4 hours and treated with ammonium chloride (0.2 mL, aqueous saturated). The mixture was diluted with dichloromethane (15 mL) and washed with brine (15 mL). The organic extract was dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by preparative reverse phase HPLC (eluting 80:20 to 5:95; water containing 0.1% trifluoroacetic acid:acetonitrile containing 0.1% trifluoroacetic acid), providing the title compound: 1H-NMR (400 MHz, CD3OD) δ 8.95 (1H, s), 8.34 (1H, d, J=7.8 Hz), 7.88 (1H, d, J=8.5 Hz), 7.70-7.66 (1H, m), 7.62-7.58 (1H, m), 7.47-7.38 (4H, m), 7.33-7.26 (4H, m), 5.76 (2H, s), 2.94 (3H, s), 2.27 (3H, s), ppm; low resolution mass spectrometry (ES+) m/z 458.9 [(M+H)+; calculated for C23H22N4O3S: 459.1].

Workup

  1. washwashed with brine (15 mL)
  2. extractionThe organic extract
  3. dry with materialwas dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative reverse phase HPLC (eluting 80:20 to 5:95; water containing 0.1% trifluoroacetic acid:acetonitrile containing 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-ce7469cc967a4a3f92c981f0088c066e
Source dataset
uspto-grants-2014_11
Patent number
US08895580B2

Reaction notes

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