Triethylamine → HCID 59367073, compound

HRID 1923989Notes

Reaction equation

HRID 1923989 reaction equation
[NH2:1][C@@H:2]([CH2:16][CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)[C:3]([NH:5][C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:4].CCN(CC)CC.S([N:37]=[N+:38]=[N-])(C(F)(F)F)(=O)=O>CO.O.C(Cl)Cl.[O-]S([O-])(=O)=O.[Cu+2]>[N:1]([C@@H:2]([CH2:16][CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)[C:3]([NH:5][C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:4])=[N+:37]=[N-:38]

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 10986786Methanesulfonyl azide, trifluoro-HCID 59367078HCID 59367078, compound

Product 1

HCID 59367073HCID 59367073, compound

Reagents, catalysts & solvents 4

HCID 24462Copper SulfateCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S)-2-amino-3-(piperidin-4-yl)-N-(quinolin-3-yl) propanamide LXXVI in a mixture of methanol (15 mL) and water (5 mL) was added Et3N (0.60 mL, 4.24 mmol) and CuSO4 (20 mg). The mixture was treated at 0° C. with freshly prepared solution of triflic azide (5.9 mmol) in DCM (10 mL). The mixture was stirred at r.t. for 48 h. The solvent was evaporated under reduced pressure and dissolved in EtOAc, washed with satd. aq. NaHCO3, water and dried over Na2SO4. The solvent was removed under vacuum to give crude (2S)-2-azido-3-(piperidin-4-yl)-N-(quinolin-3-yl) propanamide LXXVII (320 mg). ESIMS found for C17H20N6O m/z 325 (M+H).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutiondissolved in EtOAc
  3. washwashed with satd
  4. dry with materialaq. NaHCO3, water and dried over Na2SO4
  5. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-6c1989ecb490405a968d5cdcfeb425c4
Source dataset
uspto-grants-2012_05
Patent number
US08178490B2

Reaction notes

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