Triethylamine → HCID 90410866, compound

HRID 2175742Notes

Reaction equation

HRID 2175742 reaction equation
FC(F)(F)C(O)=O.[Br:8][C:9]1[CH:10]=[C:11]2[C:21](=[N:22][CH:23]=1)[NH:20][C:19](=[O:24])[C:13]1([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)[CH2:12]2.C(N(CC)CC)C.[C:32](Cl)(=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34]>C(Cl)Cl.O>[Br:8][C:9]1[CH:10]=[C:11]2[C:21](=[N:22][CH:23]=1)[NH:20][C:19](=[O:24])[C:13]1([CH2:18][CH2:17][N:16]([C:32](=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:15][CH2:14]1)[CH2:12]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 90135746HCID 90135746, compound

Product 1

HCID 90410866HCID 90410866, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
27.5 °C

Procedure

To a stirred solution of 6-bromo-1H-spiro[[1,8]naphthyridine-3,4′-piperidin]-2(4H)-one 2,2,2-trifluoroacetate (Intermediate-14) (100 mg, 0.24 mmol) in DCM (3 mL) were added triethylamine (0.1 mL, 0.72 mmol) and pivaloyl chloride (40 mg, 0.32 mmol) at 20-35° C. and the reaction mixture was allowed to stir at 20-35° C. for 16 h. Then the reaction mixture was diluted with water (30 mL) and extracted with DCM (2×30 mL). The organic layer was washed with brine (50 mL), dried over anhydrous Na2SO4 and filtered. The filtrate was rotary evaporated under vacuum to get residue which was purified by column chromatography using mixture of 60% ethyl acetate/hexane as an eluent to get the desired compound as a creamy white solid (50 mg, 55%); 1H NMR (400 MHz, DMSO-d6) δ 10.73 (s, 1H), 8.23 (d, J=1.9 Hz, 1H), 7.85 (d, J=1.5 Hz, 1H), 3.79-3.74 (m, 2H), 3.44 (t, J=10.1 Hz, 2H), 2.99 (s, 2H), 1.75-1.68 (m, 2H), 1.35-1.29 (m, 2H), 1.18 (s, 9H); ES-MS: 380.2 (M+1)+.

Workup

  1. extractionextracted with DCM (2×30 mL)
  2. washThe organic layer was washed with brine (50 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customThe filtrate was rotary evaporated under vacuum
  6. customto get residue which
  7. customwas purified by column chromatography
  8. additionmixture of 60% ethyl acetate/hexane as an eluent

Sources & evidence

ORD record
ord-c637741fbdbc4a9e9c6cff39b3b95d65
Source dataset
uspto-grants-2015_06
Patent number
US09062075B2

Reaction notes

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