Triethylamine → HCID 58739117, compound

HRID 720443Notes

Reaction equation

HRID 720443 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3[C:14](=[O:27])[N:15]([CH2:18][CH2:19][CH2:20][CH2:21][C:22]([N:24]([CH3:26])[CH3:25])=[NH:23])[CH2:16][CH2:17][C:12]=3[C:11]([C:28]([F:31])([F:30])[F:29])=[N:10]2)=[CH:5][CH:4]=1.[CH3:32][S:33](Cl)(=[O:35])=[O:34].C(N(CC)CC)C>C(Cl)Cl>[CH3:26][N:24]([CH3:25])[C:22](=[N:23][S:33]([CH3:32])(=[O:35])=[O:34])[CH2:21][CH2:20][CH2:19][CH2:18][N:15]1[CH2:16][CH2:17][C:12]2[C:11]([C:28]([F:31])([F:29])[F:30])=[N:10][N:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[C:13]=2[C:14]1=[O:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10388364HCID 10388364, compound

Product 1

HCID 58739117HCID 58739117, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-[1-(4-Methoxy-phenyl)-7-oxo-3-trifluoromethyl-1,4,5,7-tetrahydro-pyrazolo[3,4-c]pyridin-6-yl]-N,N-dimethyl-pentanamidine (0.050 g, 0.114 mmol) was dissolved in methylene chloride (10 mL). Methanesulfonyl chloride (0.1 mL, excess) and triethylamine (0.3, excess) were added to the reaction. The reaction was stirred at rt overnight, concentrated, and purified by flash chromatography using 0–100% ethyl acetate/hexanes as the eluent followed by a methanol flush. Further purification by reverse phase HPLC and freeze-drying afforded the title compound (0.120 g, 74%): 1H NMR (CHCl3) δ 7.44 (d, j=8.7 Hz, 2H), 6.95 (d, j=8.8 Hz, 2H), 3.84 (s, 3H), 3.69 (t, j=7.0 Hz, 2H), 3.52 (t, j=6.3 Hz, 2H), 3.03 (s, 3H), 3.00(s, 3H), 2.99 (s, 3H), 3.14–2.98 (m, 2H), 2.89 (t, j=7.7 Hz, 2H), 1.75–1.62 (m, 2H) ppm; Mass Spec 516.3(M+H)+.

Workup

  1. concentrationconcentrated
  2. custompurified by flash chromatography
  3. customflush
  4. customFurther purification by reverse phase HPLC
  5. customfreeze-drying

Sources & evidence

ORD record
ord-5e5ba53660f643c5b75be083aeef746f
Source dataset
uspto-grants-2006_11
Patent number
US07135469B2

Reaction notes

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