Triethylamine → HCID 90410819, compound

HRID 2175744Notes

Reaction equation

HRID 2175744 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]([NH:36][C:37](=O)[O:38]C1C=CC=CC=1)([CH3:35])([CH3:34])[CH3:33]>CS(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][N:16]([C:37]([NH:36][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:38])[CH2:15][CH2:14]1)[CH2:12]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2817207HCID 2817207, compoundHCID 90135746HCID 90135746, compound

Product 1

HCID 90410819HCID 90410819, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
70 °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) (500 mg, 1.22 mmol) in DMSO (5 mL) were added triethylamine (370 mg, 3.66 mmol) and phenyl tert-butylcarbamate (490 mg, 2.44 mmol) at 20-35° C. and the reaction mixture was allowed to stir at 70° C. for 16 h. Then the reaction mixture was diluted with water (100 mL) and extracted with DCM (2×100 mL). The organic layer was washed with brine (100 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 2% methanol/dichloromethane as an eluent to get the desired compound as an off-white solid (250 mg, 52%); 1H NMR (400 MHz, DMSO-d6) δ 10.67 (s, 1H), 8.22 (d, J=2.5 Hz, 1H), 7.87 (d, J=2.0 Hz, 1H), 5.74 (d, J=10.5 Hz, 1H), 3.52 (dt, J=4.4 Hz, 9.5 Hz, 2H), 3.16-3.08 (m, 2H), 2.95 (s, 2H), 1.73-1.65 (m, 2H), 1.34-1.23 (m, 11H); LC-MS: 397.2 (M+1)+.

Workup

  1. extractionextracted with DCM (2×100 mL)
  2. washThe organic layer was washed with brine (100 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 2% methanol/dichloromethane as an eluent

Sources & evidence

ORD record
ord-73062cb7d7d641b0897a11ccfbcf5ee9
Source dataset
uspto-grants-2015_06
Patent number
US09062075B2

Reaction notes

Loading…