Water → HCID 52950782, compound

HRID 1521866Notes

Reaction equation

HRID 1521866 reaction equation
[N:1]1([C:7]([C:9]2[C:10]3[CH2:27][S:26](=[O:29])(=[O:28])[C:25]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[C:11]=3[N:12]([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[N:13]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:37][S:38](Cl)(=[O:40])=[O:39].O>C1COCC1>[CH3:37][S:38]([N:17]1[CH2:18][CH2:19][CH:14]([N:12]2[C:11]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=4[S:26](=[O:29])(=[O:28])[CH2:27][C:10]=3[C:9]([C:7]([N:1]3[CH2:2][CH2:3][O:4][CH2:5][CH2:6]3)=[O:8])=[N:13]2)[CH2:15][CH2:16]1)(=[O:40])=[O:39]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66578873HCID 66578873, compound

Product 1

HCID 52950782HCID 52950782, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(morpholin-4-ylcarbonyl)-1-piperidin-4-yl-1,4-dihydrothiochromeno[4,3-c]pyrazole 5,5-dioxide (30 mg, 0.066 mmol) in THF (10 mL) is added triethylamine (40 □l, 0.26 mmol) and the reaction mass is cooled to 0° C. after which methane sulfonyl chloride (0.01 mL, 0.099 mmol) is slowly added. The reaction mixture is slowly warmed to RT then stirred for 12 h. After this time, water is added to the reaction mixture that is then extracted with EtOAc. The organic layer is separated, dried under sodium sulphate and concentrated under reduced pressure. Compound is then purified by neutral alumina column chromatography (0.2% MeOH in chloroform) to afford the title compound as an off white solid. 1H NMR (DMSO-d6, 400 MHz): δ 8.20-8.18 (d, J=7.0 Hz, 1H), 7.78-7.75 (m, 1H), 7.67-7.64 (m, 1H), 7.52-7.49 (m, 1H), 4.70 (m, 3H), 4.18 (m, 2H), 4.05 (m, 2H), 3.81 (s, 6H), 2.99-2.94 (t, J=11.4 Hz, 2H), 2.80 (s, 3H), 2.47-2.42 (m, 2H), 2.24-2.18 (m, 2H). MS (ESI+): 495.0. HPLC (max plot) 93.19%; Rt 3.18 min.

Workup

  1. additionis slowly added
  2. extractionis then extracted with EtOAc
  3. customThe organic layer is separated
  4. customdried under sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customCompound is then purified by neutral alumina column chromatography (0.2% MeOH in chloroform)

Sources & evidence

ORD record
ord-172965a430684234bc843905de1696ad
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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