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Quinaldic Acid → N-(5-Bromo-8-morpholinoimidazo[1,2-a]pyrazin-2-yl)quinoline-2-carboxamide

HRID 1772636
Notes
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Reaction equation

HRID 1772636 reaction equation
[C:1]([OH:13])(=O)[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[Br:47][C:48]1[N:53]2[CH:54]=[C:55]([NH2:57])[N:56]=[C:52]2[C:51]([N:58]2[CH2:63][CH2:62][O:61][CH2:60][CH2:59]2)=[N:50][CH:49]=1>C(Cl)Cl>[Br:47][C:48]1[N:53]2[CH:54]=[C:55]([NH:57][C:1]([C:2]3[CH:11]=[CH:10][C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[N:3]=3)=[O:13])[N:56]=[C:52]2[C:51]([N:58]2[CH2:59][CH2:60][O:61][CH2:62][CH2:63]2)=[N:50][CH:49]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7124Quinaldic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 1177280545-Bromo-8-morpholinoimidazo[1,2-a]pyrazin-2-amine

Product 1

HCID 117728149N-(5-Bromo-8-morpholinoimidazo[1,2-a]pyrazin-2-yl)quinoline-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of quinaldic acid (236 mg, 1.36 mmol) in DCM (10 mL) were added HATU (519 mg, 1.36 mmol) and DIEA (201 μL, 1.15 mmol) at 0° C. The reaction mixture was stirred for 0.5 h at 0° C. and treated with compound 21b (313 mg, 1.04 mmol). The resulting mixture was stirred at rt overnight. The solids formed were collected by filtration, and the organic phase was washed with saturated aqueous NH4Cl (20 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography on silica gel (9:1 DCM/EtOAc) to give compound 21c. Mass Spectrum (LCMS, ESI pos.) Calcd. for C20H17BrN6O2: 453.0 (M+H). Found 453.1.

Workup

  1. stirringThe resulting mixture was stirred at rt overnight
  2. customThe solids formed
  3. filtrationwere collected by filtration
  4. washthe organic phase was washed with saturated aqueous NH4Cl (20 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by flash column chromatography on silica gel (9:1 DCM/EtOAc)

Sources & evidence

ORD record
ord-10484760c5034bff830bcc821c9f9bec
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09249163B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes