Triethylamine → HCID 66958189, compound

HRID 1364022Notes

Reaction equation

[CH3:1][C:2]([NH2:19])([CH3:18])[CH2:3][NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16].C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>ClCCl>[CH3:18][C:2]([NH:19][S:28]([CH3:27])(=[O:30])=[O:29])([CH3:1])[CH2:3][NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16]

Participants

Conditions

Temperature: 0 °C

Procedure

Under a nitrogen atmosphere, a suspension of 2-methyl-N1-(3-nitroquinolin-4-yl)propane-1,2-diamine (93 g, 358 mmol) and triethylamine (100 mL, 717 mmol) in anhydrous dichloromethane (1 L) was cooled to 0° C. Methanesulfonyl chloride (27.7 mL, 358 mmol) was added over a period of 20 minutes. The reaction was allowed to warm to ambient temperature and stirred overnight. Additional methanesulfonyl chloride (9.2 mL) was added over a period of five minutes, and the reaction was stirred for an additional day. Additional methanesulfonyl chloride (2.0 mL) was added, and the reaction was stirred for two hours. The solvent was removed under reduced pressure, and the residue was triturated with water (800 mL) at 50° C., isolated by filtration, and washed with water to provide 116 g of N-{1,1-dimethyl-2-[(3-nitroquinolin-4-yl)amino]ethyl}methanesulfonamide as a yellow powder.

Workup

temperatureto warm to ambient temperature
stirringthe reaction was stirred for an additional day
stirringthe reaction was stirred for two hours
customThe solvent was removed under reduced pressure
customthe residue was triturated with water (800 mL) at 50° C.
customisolated by filtration
washwashed with water

Sources & evidence

ORD record: ord-492a40ce9255450e891087ab1ff5e5e3
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07888349B2

Reaction notes

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