Triethylamine → HCID 118274222, compound

HRID 522205Notes

Reaction equation

HRID 522205 reaction equation
Cl.Cl.[CH2:3]([CH:5]1[N:22]([CH3:23])[CH:21]=[C:8]2[C:9]3[CH:19]=[C:18]([F:20])[CH:17]=[C:11]4[CH:12]=[CH:13][C:14](=[N:15][NH:16][C:7]2=[C:6]1[C:24]1[CH2:25][CH2:26][NH:27][CH2:28][CH:29]=1)[C:10]=34)[CH3:4].C(N(CC)CC)C.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>ClCCl>[CH2:3]([CH:5]1[N:22]([CH3:23])[CH:21]=[C:8]2[C:9]3[CH:19]=[C:18]([F:20])[CH:17]=[C:11]4[CH:12]=[CH:13][C:14](=[N:15][NH:16][C:7]2=[C:6]1[C:24]1[CH2:25][CH2:26][N:27]([S:38]([CH3:37])(=[O:40])=[O:39])[CH2:28][CH:29]=1)[C:10]=34)[CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 118274282HCID 118274282, compound

Product 1

HCID 118274222HCID 118274222, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of Example 9 (35 mg, 0.08 mmol) in dichloromethane (5 mL) was added triethylamine (0.07 mL, 0.482 mmol) and methanesulfonyl chloride (14 mg, 0.121 mmol). The mixture was stirred at room temperature for 2 hours, and purified by flash chromatography on silica gel (Teledyne CombiFlash Rf, 0-15% methanol in 2:1 ethyl acetate/hexane) to provide the title compound. 1H NMR (400 MHz, CD3OD): δ 0.81-0.86 (m, 3H), 1.22-1.30 (m, 1H), 1.37-1.45 (m, 1H), 2.62-2.69 (m, 1H), 2.73-2.81 (m, 1H), 2.88 (s, 3H), 2.98 (s, 3H), 3.36-3.41 (m, 1H), 3.42-3.48 (m, 1H), 3.96 (dd, J=5.80, 3.05 Hz, 2H), 4.28 (dd, J=9.00, 5.65 Hz, 1H), 6.11 (s, 1H), 7.21-7.29 (m, 2H), 7.35 (d, J=5.49 Hz, 1H), 7.77 (dd, J=10.68, 2.75 Hz, 1H), 8.22 (d, J=5.19 Hz, 1H), 11.51 (s, 1H). MS (ESI+) m/z 441 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-dc0b6711a20647868b8eb29fd2dd2790
Source dataset
uspto-grants-2016_05
Patent number
US09328112B2

Reaction notes

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