N-bromobutanimide → HCID 46945342, compound

HRID 2047206Notes

Reaction equation

HRID 2047206 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[CH:13]=[C:12]([NH2:14])[N:11]3[N:15]=[CH:16][C:17]([C:18]4[CH:19]=[N:20][C:21]5[C:26]([CH:27]=4)=[CH:25][CH:24]=[CH:23][CH:22]=5)=[C:10]3[N:9]=2)[CH2:3][CH2:2]1.[Br:28]N1C(=O)CCC1=O>CC#N>[Br:28][C:13]1[C:8]([CH2:7][N:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[N:9][C:10]2[N:11]([N:15]=[CH:16][C:17]=2[C:18]2[CH:19]=[N:20][C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:12]=1[NH2:14]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 46945343HCID 46945343, compound

Product 1

HCID 46945342HCID 46945342, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To crude 5-(morpholinomethyl)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-7-amine (44 mg) in CH3CN (8 mL) was added N-bromosuccinimide (22 mg, 0.12 mmol), followed by additional CH3CN (4 mL). The reaction was then stirred at room temperature for 30 minutes, at which time LC/MS analysis confirmed full conversion of the starting material to the product. The reaction mixture was concentrated in vacuo and purified by preparative HPLC to give 6-bromo-5-(morpholinomethyl)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-7-amine as a yellow solid (8.7 mg, 0.02 mmol, 7% over three steps). LCMS: 0.82 mins, m/z=439.0 and 441.0 (MH+).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-b1fac33f84b4414597e1621b9224dec0
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

Loading…