N-methyl-2-pyrrolidone → HCID 71116989, compound

HRID 629889Notes

Reaction equation

HRID 629889 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].CN1C(=O)CCC1.[CH3:13][C:14]([CH3:34])([CH3:33])[CH2:15][N:16]1[C:24]2[C:19](=[N:20][C:21]([CH:25]3[CH2:30][CH2:29][CH2:28][NH:27][CH2:26]3)=[CH:22][CH:23]=2)[N:18]([CH3:31])[C:17]1=[O:32].CCN(C(C)C)C(C)C>CO>[CH3:13][C:14]([CH3:34])([CH3:33])[CH2:15][N:16]1[C:24]2[C:19](=[N:20][C:21]([CH:25]3[CH2:30][CH2:29][CH2:28][N:27]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:26]3)=[CH:22][CH:23]=2)[N:18]([CH3:31])[C:17]1=[O:32]

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 71136197HCID 71136197, compound

Product 1

HCID 71116989HCID 71116989, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a flask was added methanesulfonyl chloride (3.74 mg, 0.033 mmol), NMP (0.5 mL), then (18-2) (7.6 mg, 0.025 mmol), & DIPEA (40 μl, 0.229 mmol). The reaction mixture was stirred at room temperature for 3 hours, then diluted with MeOH & purified by reverse phase chromatography (5-95% CH3CN:0.1% TFA in H2O) to give 1-(2,2-Dimethylpropyl)-3-methyl-5-[1-(methylsulfonyl)piperidin-3-yl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (19-1). HRMS (M+H)+: observed=381.1956, calculated=381.1955. 1H NMR (499 MHz, DMSO): δ 7.48 (d, J=7.9 Hz, 1H); 7.02 (d, J=7.9 Hz, 1H); 3.71-3.68 (m, 1H); 3.64-3.56 (m, 3H); 3.34 (s, 3H); 2.93-2.83 (m, 5H); 2.78-2.72 (m, 1H); 2.00-1.92 (m, 1H); 1.89-1.82 (m, 1H); 1.76-1.60 (m, 2H); 0.95 (s, 9H).

Workup

  1. custompurified by reverse phase chromatography (5-95% CH3CN:0.1% TFA in H2O)

Sources & evidence

ORD record
ord-9d92bff665be46e2ba2da9b5868257fe
Source dataset
uspto-grants-2016_04
Patent number
US09315518B2

Reaction notes

Loading…