2,6-Lutidine → HCID 22660825, compound

HRID 392983Notes

Reaction equation

HRID 392983 reaction equation
[C:1]([CH2:3][CH2:4][NH:5][C:6]([C:8]1[CH:9]=[C:10]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])=[CH:19][CH:18]=3)[N:14]([CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)[C:11]2=[N:12][CH:13]=1)=O)#[N:2].[N-:37]=[N+:38]=[N-:39].[Na+].N1C(C)=CC=CC=1C.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O>ClCCl>[C:27]([Si:24]([CH3:25])([CH3:26])[O:23][C:20]1[CH:19]=[CH:18][C:17]([C:15]2[N:14]([CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)[C:11]3=[N:12][CH:13]=[C:8]([C:6]4[N:5]([CH2:4][CH2:3][C:1]#[N:2])[N:39]=[N:38][N:37]=4)[CH:9]=[C:10]3[N:16]=2)=[CH:22][CH:21]=1)([CH3:30])([CH3:28])[CH3:29]

Participants

6

Reactant 4

HCID 79372,6-LutidineHCID 33557Sodium AzideHCID 67749Trifluoromethanesulfonic anhydrideHCID 86588759HCID 86588759, compound

Product 1

HCID 22660825HCID 22660825, compoundYield 18.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of intermediate 61 (250 mg, 0.5 mmol), sodium azide (33 mg, 0.5 mmol), and 2,6-lutidine (116 μL, 1.0 mmol) in dichloromethane (3 mL) was cooled to 0° C. and trifluoromethanesulfonic anhydride (84 μL, 0.5 mmol) from a freshly opened ampule was added under a nitrogen atmosphere. The reaction mixture was allowed to warm up slowly to rt over 2 h and stirring continued for 20 h at which point dichloromethane was added (25 mL). The resulting organic phase was washed with saturated NaHCO3 (1×20 mL), dried (Na2SO4), and concentrated on a rotary evaporator. The foamy residue was purified by reverse phase HPLC (C18 column, water/acetonitrile gradient containing 0.05% trifluoroacetic acid) to afford intermediate 62 as a white solid (48 mg, 18%). ESI-MS m/e 529.1 (M+1).

Workup

  1. additionwas added (25 mL)
  2. washThe resulting organic phase was washed with saturated NaHCO3 (1×20 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated on a rotary evaporator
  5. customThe foamy residue was purified by reverse phase HPLC (C18 column, water/acetonitrile gradient containing 0.05% trifluoroacetic acid)

Sources & evidence

ORD record
ord-f264895dffbd4a518834064f24465bb4
Source dataset
uspto-grants-2004_10
Patent number
US06803374B2

Reaction notes

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