Methanesulfonyl chloride → HCID 86682251, compound

HRID 1428380Notes

Reaction equation

HRID 1428380 reaction equation
[Cl:1][C:2]1[C:6]([N:7]([CH2:13][C:14]#[CH:15])[C:8](=[O:12])[CH2:9][NH:10][CH3:11])=[CH:5][N:4]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[N:3]=1.[CH3:22][S:23](Cl)(=[O:25])=[O:24].C(N(C(C)C)CC)(C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[C:6]([N:7]([CH2:13][C:14]#[CH:15])[C:8](=[O:12])[CH2:9][N:10]([CH3:11])[S:23]([CH3:22])(=[O:25])=[O:24])=[CH:5][N:4]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[N:3]=1

Participants

6

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 86682249HCID 86682249, compound

Product 1

HCID 86682251HCID 86682251, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-2-(methylamino)-N-(prop-2-yn-1-yl)acetamide (0.100 g, 0.329 mmol) in DCM (0.65 ml) was added methanesulfonyl chloride (0.057 g, 0.494 mmol) followed by diisopropylethylamine (0.11 ml, 0.658 mmol) and the reaction was stirred at room temperature for 24 h. The reaction mixture was poured into a solution of saturated NaHCO3 and subsequently extracted with DCM. The organic layers were combined and concentrated, and the residue was purified using silica gel chromatography (50-100% EtOAc/hexanes) to afford the title compound as a yellow solid (0.091 g, 0.238 mmol, 72%): (IR thin film) 1678 cm−1; 1H NMR (400 MHz, CDCl3) δ 8.97 (d, J=2.6 Hz, 1H), 8.65 (dd, J=4.8, 1.3 Hz, 1H), 8.15 (s, 1H), 8.04 (ddd, J=8.3, 2.7, 1.4 Hz, 1H), 7.48 (dd, J=8.4, 4.7 Hz, 1H), 3.77 (hept, J=6.9 Hz, 2H), 3.05 (s, 2H), 3.01 (s, 3H), 2.87 (s, 3H), 2.31 (t, J=2.5 Hz, 1H); ESIMS m/z 382 ([M+H]+).

Workup

  1. extractionsubsequently extracted with DCM
  2. concentrationconcentrated
  3. customthe residue was purified

Sources & evidence

ORD record
ord-72e3d0ef2af44f358947cfd76918d00a
Source dataset
uspto-grants-2015_01
Patent number
US08937083B2

Reaction notes

Loading…