Triethylamine → HCID 90412169, compound

HRID 2175746Notes

Reaction equation

HRID 2175746 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.[N:32]1([C:36](OC2C=CC=CC=2)=[O:37])[CH2:35][CH2:34][CH2:33]1>CS(C)=O>[N:32]1([C:36]([N:16]2[CH2:17][CH2:18][C:13]3([CH2:12][C:11]4[C:21](=[N:22][CH:23]=[C:9]([Br:8])[CH:10]=4)[NH:20][C:19]3=[O:24])[CH2:14][CH2:15]2)=[O:37])[CH2:35][CH2:34][CH2:33]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12025112HCID 12025112, compoundHCID 90135746HCID 90135746, compound

Product 1

HCID 90412169HCID 90412169, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

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) (600 mg, 1.47 mmol) in DMSO (5 mL) was added triethylamine (0.60 mL, 4.40 mmol) at 0° C. and the mixture was stirred at the same temperature for 15 min. Then phenyl azetidine-1-carboxylate (J) (520 mg, 2.93 mmol) was added and the reaction mixture was allowed to stir at 100° C. for 24 h. The reaction mixture was cooled to 20-35° C., diluted with ice cold water (30 mL) and extracted with ethyl acetate (2×50 mL). The organic layer was washed with brine (30 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 3% MeOH/DCM as an eluent to get the desired compound as a brown solid (180 mg, 32%); 1H NMR (400 MHz, DMSO-d6) δ 10.70 (s, 1H), 8.22 (d. J=1.5 Hz, 1H), 7.86 (d, J=1.9 Hz, 1H), 3.86 (t, J=7.8 Hz, 4H), 3.43-3.36 (m, 2H), 3.21-3.13 (m, 2H), 2.96 (s, 2H), 2.18-2.10 (m, 2H), 1.73-1.67 (m, 2H), 1.34-1.23 (m, 2H).

Workup

  1. stirringto stir at 100° C. for 24 h
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. washThe organic layer was washed with brine (30 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customThe filtrate was rotary evaporated under vacuum
  7. customto get residue
  8. customwhich was purified by column chromatography
  9. additionmixture of 3% MeOH/DCM as an eluent

Sources & evidence

ORD record
ord-76fab3b509f442fab4c83e2946b00a29
Source dataset
uspto-grants-2015_06
Patent number
US09062075B2

Reaction notes

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