Triethylamine → HCID 118274125, compound

HRID 522219Notes

Reaction equation

HRID 522219 reaction equation
[F:1][C:2]1[C:11]2=[CH:12][C:13]([F:15])=[CH:14][C:9]3=[C:10]2[C:4](=[N:5][NH:6][C:7]2[C:8]3=[CH:16][N:17]([CH3:26])[CH2:18][C:19]=2[C:20]2[CH2:21][CH2:22][NH:23][CH2:24][CH:25]=2)[CH:3]=1.C(N(CC)CC)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>ClCCl>[F:1][C:2]1[C:11]2=[CH:12][C:13]([F:15])=[CH:14][C:9]3=[C:10]2[C:4](=[N:5][NH:6][C:7]2[C:8]3=[CH:16][N:17]([CH3:26])[CH2:18][C:19]=2[C:20]2[CH2:21][CH2:22][N:23]([S:35]([CH3:34])(=[O:37])=[O:36])[CH2:24][CH:25]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 118274132HCID 118274132, compound

Product 1

HCID 118274125HCID 118274125, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of Example 48 (60 mg, 0.17 mmol) in dichloromethane (5 mL) was added triethylamine (0.1 mL, 0.68 mmol) and methanesulfonyl chloride (30 mg, 0.25 mmol) and the mixture was stirred at room temperature overnight. Purification by flash chromatography on silica gel (Teledyne CombiFlash Rf, 0-15% methanol in 2:1 ethyl acetate/hexane) provided the title compound. 1H NMR (400 MHz, DMSO-d6): δ 2.71 (s, 1H), 2.89 (s, 3H), 2.97 (s, 3H), 3.36-3.41 (m, 2H), 3.94-3.95 (m, 2H), 4.08 (s, 2H), 5.90 (s, 1H), 7.28-7.32 (m, 1H), 7.39 (dd, J=9.16, 5.49 Hz, 1H), 7.63-7.67 (m, 1H), 8.27 (d, J=4.88 Hz, 1H), 11.72 (s, 1H). MS (ESI+) m/z 411 (M+H)+.

Workup

  1. customPurification by flash chromatography on silica gel (Teledyne CombiFlash Rf, 0-15% methanol in 2:1 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f2783736ce164509a58618a9bda9ad5e
Source dataset
uspto-grants-2016_05
Patent number
US09328112B2

Reaction notes

Loading…