N-Bromosuccinamide → HCID 117728336, compound

HRID 1772659Notes

Reaction equation

HRID 1772659 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:12][C:13]1[N:14]=[C:15]2[C:20]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[N:19][CH:18]=[CH:17][N:16]2[CH:27]=1.[Br:28]NC(=O)CCC(N)=O>C(Cl)Cl>[Br:28][C:17]1[N:16]2[CH:27]=[C:13]([CH2:12][O:11][C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:1]=3)[N:14]=[C:15]2[C:20]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[N:19][CH:18]=1

Participants

4

Reactant 2

HCID 9834204N-BromosuccinamideHCID 1177283094-(2-((Quinolin-2-yloxy)methyl)imidazo[1,2-a]pyrazin-8-yl)morpholine

Product 1

HCID 117728336HCID 117728336, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of compound 31a (5.0 g, 14 mmol) and N-bromosuccinamide (2.5 g, 14 mmol) in DCM (300 mL) at 0° C. was allowed to stir at rt for 10 min. The reaction mixture was diluted with DCM (600 mL) and washed with saturated NaHCO3 (500 mL) and brine (500 mL). The DCM layer was separated, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue obtained was triturated with EtOAc to give compound 31b as a white solid. Mass Spectrum (LCMS, ESI pos.): Calcd. for C20H18BrN5O2: 440.1 (M+H). found: 440.0.

Workup

  1. washwashed with saturated NaHCO3 (500 mL) and brine (500 mL)
  2. customThe DCM layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained
  7. customwas triturated with EtOAc

Sources & evidence

ORD record
ord-35cc242a72f34dd89640cbe161074c10
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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