Diisopropylethylamine → HCID 71533634, compound

HRID 1774819Notes

Reaction equation

HRID 1774819 reaction equation
FC(F)(F)C(O)=O.[CH2:8]1[C:11]2([CH2:14][NH:13][CH2:12]2)[CH2:10][N:9]1[C:15]1[N:20]=[C:19]([C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[N:27]([CH3:31])[C:26](=[O:32])[CH2:25][CH2:24]3)[CH:18]=[N:17][CH:16]=1.[CH3:33][O:34][C:35]1[CH:39]=[C:38]([C:40](O)=[O:41])[O:37][N:36]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl.CCOC(C)=O>[CH3:33][O:34][C:35]1[CH:39]=[C:38]([C:40]([N:13]2[CH2:12][C:11]3([CH2:10][N:9]([C:15]4[N:20]=[C:19]([C:21]5[CH:22]=[C:23]6[C:28](=[CH:29][CH:30]=5)[N:27]([CH3:31])[C:26](=[O:32])[CH2:25][CH2:24]6)[CH:18]=[N:17][CH:16]=4)[CH2:8]3)[CH2:14]2)=[O:41])[O:37][N:36]=1

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 3277173-Methoxy-1,2-oxazole-5-carboxylic acidHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 86679139HCID 86679139, compound

Product 1

HCID 71533634HCID 71533634, compoundYield 22.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-(6-(2,6-diazaspiro[3.3]heptan-2-yl)pyrazin-2-yl)-1-methyl-3,4-dihydroquinolin-2(1H)-one 2,2,2-trifluoroacetate (intermediate A-36, 0.030 g, 0.067 mmol) in DCM (1 mL) were added 3-methoxyisoxazole-5-carboxylic acid (0.014 g, 0.1 mmol) and TBTU (0.024 g, 0.073 mmol) followed by Hünig's base (0.022 g, 0.167 mmol) and the reaction mixture was stirred at room temperature over night. The reaction mixture was diluted with EtOAc, poured into sat. NaHCO3 solution (5 mL) and extracted with EtOAc (2×10 mL). Combined organics were dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 5% MeOH-DCM gradient to give the title compound (0.007 g, 20%) as a yellow solid. MS: 461.3 (M+H+).

Workup

  1. extractionextracted with EtOAc (2×10 mL)
  2. dry with materialCombined organics were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue was purified by silica gel flash chromatography
  6. washeluting with a 0 to 5% MeOH-DCM gradient

Sources & evidence

ORD record
ord-629a4ef1298a4bdf96dc0545f8ab4a8e
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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