Diisopropylethylamine → HCID 86656450, compound

HRID 1028049Notes

Reaction equation

HRID 1028049 reaction equation
FC(F)(F)S(O[C:7]1[C:16]2[C:11](=[CH:12][N:13]=[C:14]([Cl:17])[CH:15]=2)[N:10]=[CH:9][CH:8]=1)(=O)=O.[NH:20]1[CH2:25][CH2:24][CH2:23][C@H:22]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:21]1.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:17][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][N:13]=1)[N:10]=[CH:9][CH:8]=[C:7]2[N:20]1[CH2:25][CH2:24][CH2:23][C@H:22]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:31])([CH3:30])[CH3:32])[CH2:21]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1514171tert-butyl N-[(3S)-piperidin-3-yl]carbamateHCID 58387621HCID 58387621, compound

Product 1

HCID 86656450HCID 86656450, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-chloro-1,7-naphthyridin-4-yl trifluoromethanesulfonate (1.0 equiv.), (S)-tert-butyl piperidin-3-ylcarbamate (1.0 equiv.) and DIEA (1.5 equiv.) in CH2Cl2 (0.3 M) was stirred at rt for 120 hours. The solution was partitioned between EtOAc and Na2CO3(sat.). Upon separation, the organic layer was washed with NaCl(sat.), dried over MgSO4, concentrated and purified by silica gel chromatography (EtOAc eluant) to yield (S)-tert-butyl 1-(6-chloro-1,7-naphthyridin-4-yl)piperidin-3-ylcarbamate (61%). LC/MS=363.2 (M+H), LC=2.47 min.

Workup

  1. customThe solution was partitioned between EtOAc and Na2CO3(sat.)
  2. customUpon separation
  3. washthe organic layer was washed with NaCl(sat.)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. custompurified by silica gel chromatography (EtOAc eluant)

Sources & evidence

ORD record
ord-341271ffdb7d4f189531f49b40e1c5fb
Source dataset
uspto-grants-2014_05
Patent number
US08735424B2

Reaction notes

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