N-methyl-2-pyrrolidone → HCID 68245104, compound

HRID 515233Notes

Reaction equation

HRID 515233 reaction equation
[F:1][C:2]1([F:30])[CH2:4][CH:3]1[CH2:5][N:6]1[C:14]2[C:9](=[N:10][C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]4[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)[CH:16]=3)=[CH:12][CH:13]=2)[N:8]([CH3:27])[S:7]1(=[O:29])=[O:28].CN1C(=O)CCC1.CCN(C(C)C)C(C)C.[CH3:47][S:48](Cl)(=[O:50])=[O:49]>CO>[F:30][C:2]1([F:1])[CH2:4][CH:3]1[CH2:5][N:6]1[C:14]2[C:9](=[N:10][C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]4[CH2:26][CH2:25][N:24]([S:48]([CH3:47])(=[O:50])=[O:49])[CH2:23][CH2:22]4)[CH:16]=3)=[CH:12][CH:13]=2)[N:8]([CH3:27])[S:7]1(=[O:29])=[O:28]

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 86687903HCID 86687903, compound

Product 1

HCID 68245104HCID 68245104, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a vial was added 1-[(2,2-difluorocyclopropyl)methyl]-3-methyl-5-(3-piperidin-4-ylphenyl)-1,3-dihydro[1,2,5]thiadiazolo[3,4-b]pyridine 2,2-dioxide (31-3) (0.030 g, 0.064 mmol), NMP (1 mL), DIPEA (0.060 mL, 0.344 mmol), and finally methanesulfonyl chloride (0.0374 mL, 0.480 mmol). The reaction mixture was then permitted to stir at room temperature for 1 hour. The crude reaction mixture was then diluted with methanol, then filtered. Purification of crude reaction mixture by reverse phase chromatography (Waters Sunfire MSC18, 10% acetonitrile/0.1% trifluoroacetic acid/water→100% acetonitrile/0.1% trifluoroacetic acid/water) to give 1-[(2,2-difluorocyclopropyl)methyl]-3-methyl-5-{3-[1-(methylsulfonyl)piperidin-4-yl]phenyl}-1,3-dihydro[1,2,5]thiadiazolo[3,4-b]pyridine 2,2-dioxide (31-4) as a tan solid. HRMS (M+H)+: observed=513.1430, calculated=513.1436.

Workup

  1. customThe crude reaction mixture
  2. filtrationfiltered
  3. customPurification of crude
  4. customreaction mixture by reverse phase chromatography (Waters Sunfire MSC18, 10% acetonitrile/0.1% trifluoroacetic acid/water→100% acetonitrile/0.1% trifluoroacetic acid/water)

Sources & evidence

ORD record
ord-0dd4d7d3697849629e32f68b64059ba2
Source dataset
uspto-grants-2015_08
Patent number
US09108937B2

Reaction notes

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