Benzyl Bromide → 6-Benzyl-2-(4-(2,4-difluorophenoxy)piperidin-1-yl)-3-(isopropylamino)pyrido[3,4-b]pyrazin-6-ium bromide

HRID 713219Notes

Reaction equation

HRID 713219 reaction equation
[F:1][C:2]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[N:12]=[C:13]3[CH:24]=[CH:23][N:22]=[CH:21][C:14]3=[N:15][C:16]=2[NH:17][CH:18]([CH3:20])[CH3:19])[CH2:7][CH2:6]1.[CH2:30]([Br:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(#N)C>[Br-:37].[CH2:30]([N+:22]1[CH:23]=[CH:24][C:13]2[C:14](=[N:15][C:16]([NH:17][CH:18]([CH3:20])[CH3:19])=[C:11]([N:8]3[CH2:7][CH2:6][CH:5]([O:4][C:3]4[CH:25]=[CH:26][C:27]([F:29])=[CH:28][C:2]=4[F:1])[CH2:10][CH2:9]3)[N:12]=2)[CH:21]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 90037662HCID 90037662, compound

Product 1

HCID 1181593286-Benzyl-2-(4-(2,4-difluorophenoxy)piperidin-1-yl)-3-(isopropylamino)pyrido[3,4-b]pyrazin-6-ium bromideYield 100.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a yellow-orange suspension of 2-(4-(2,4-difluorophenoxyl)piperidin-1-yl)-N-isopropylpyrido[3,4-b]pyrazin-3-amine (5.1 g, 12.77 mmol) in ACN (63.8 mL) was added benzyl bromide (2.184 g, 12.77 mmol) over 1 minute at 23° C. The mixture was stirred at 80° C. for 4 h to furnish a red-brown solution, cooled to 23° C., and then concentrated via rotary evaporation to give 6-benzyl-2-(4-(2,4-difluorophenoxyl)piperidin-1-yl)-3-(isopropylamino)pyrido[3,4-b]pyrazin-6-ium bromide (7.30 g) as a red-brown solid, which was used directly in the next step without further purification.

Workup

  1. customto furnish a red-brown solution
  2. temperaturecooled to 23° C.
  3. concentrationconcentrated via rotary evaporation

Sources & evidence

ORD record
ord-283abe37bad94c1da0b8605dd6596fc5
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

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