Hydrochloric Acid → HCID 66580548, compound

HRID 1521879Notes

Reaction equation

HRID 1521879 reaction equation
COC[N:4]1[C:9]2[C:10]([C:19]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[O:20])=[N:11][N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:8]=2[C:7]2[CH:27]=[CH:28][CH:29]=[CH:30][C:6]=2[S:5]1(=[O:32])=[O:31].Cl.C(Cl)Cl.C([O-])(O)=O.[Na+]>O1CCOCC1>[N:21]1([C:19]([C:10]2[C:9]3[NH:4][S:5](=[O:31])(=[O:32])[C:6]4[CH:30]=[CH:29][CH:28]=[CH:27][C:7]=4[C:8]=3[N:12]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:11]=2)=[O:20])[CH2:22][CH2:23][O:24][CH2:25][CH2:26]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 66579030HCID 66579030, compound

Product 1

HCID 66580548HCID 66580548, compoundYield 10.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-(methoxymethyl)-3-(morpholin-4-ylcarbonyl)-1-phenyl-1,4-dihydropyrazolo[4,3-c][1,2]benzothiazine 5,5-dioxide (85 mg; 0.19 mmol; 1.00 eq.) in 1,4-dioxane (3 mL) is added HCl (0.75 mL; 1 M; 0.75 mmol; 4.00 eq.) after which reaction mixture is stirred at 100° C. for 90 min under microwave irradiation (*2). DCM is added to the reaction mixture that is neutralized to pH 6 with NaHCO3, extracted with DCM, dried over MgSO4 and purified by MD-Autoprep to give 8 mg (10%) of the title compound as an off white solid. 1H NMR (300 MHz, DMSO-d6): δ 10.94 (s, 1H), 8.00-7.91 (m, 1H), 7.71-7.50 (m, 7H), 6.99-6.86 (m, 1H), 3.83-3.55 (m, 8H). HPLC (max plot) 97.4%; Rt 3.27 min. MS (ESI+) 411.2.

Workup

  1. customafter which reaction mixture
  2. extractionextracted with DCM
  3. dry with materialdried over MgSO4
  4. custompurified by MD-Autoprep

Sources & evidence

ORD record
ord-5524df0b263b42e195d2d134ccc0cfc9
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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