2,6-Lutidine → HCID 89690301, compound

HRID 877582Notes

Reaction equation

HRID 877582 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([NH:10][C:11]3[N:16]=[CH:15][C:14]([C:17]4[O:21][C:20]([CH:22]([NH:32]C(=O)OC(C)(C)C)[CH2:23][O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])=[N:19][N:18]=4)=[C:13]([NH:40][CH:41]([CH3:43])[CH3:42])[CH:12]=3)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.N1C(C)=CC=CC=1C.[Si](OS(C(F)(F)F)(=O)=O)(C(C)(C)C)(C)C>C(Cl)Cl>[NH2:32][CH:22]([C:20]1[O:21][C:17]([C:14]2[C:13]([NH:40][CH:41]([CH3:43])[CH3:42])=[CH:12][C:11]([NH:10][C:7]3[CH:8]=[CH:9][C:4]4[N:3]=[CH:2][S:1][C:5]=4[CH:6]=3)=[N:16][CH:15]=2)=[N:18][N:19]=1)[CH2:23][O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 89697669HCID 89697669, compound

Product 1

HCID 89690301HCID 89690301, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

tert-butyl (1-(5-(6-(benzo[d]thiazol-6-ylamino)-4-(isopropylamino)pyridin-3-yl)-1,3,4-oxadiazol-2-yl)-2-((tert-butyldimethylsilyl)oxy)ethyl)carbamate (56) (200 mg, 0.3 mmol) was dissolved in DCM (10 mL), cooled to −10° C. Added 2,6-lutidine (1.9 mmol, 6 equiv.) and stirred for 15 min. Added TBDMS-Triflate (1.6 mmol, 5 equiv.) in portions, dropwise to the reaction mixture and stirred at −10° C. for 30 min. Gradually, the reaction temperature was raised to room temperature and stirred for 30 min. Diluted the reaction mixture using DCM and quenched by addition of 5% citric acid solution. Extracted the reaction mixture in DCM. The organic layer was collected, dried over Na2SO4, filtered and concentrated. The crude material was purified by column chromatography through silica gel and MeOH: DCM as eluent to provide the desired compound, 5-(5-(1-amino-2-((tert-butyldimethylsilyl)oxy)ethyl)-1,3,4-oxadiazol-2-yl)-N2-(benzo[d]thiazol-6-yl)-N4-isopropylpyridine-2,4-diamine LC/MS: Acquity BEH C18 2.1×50 mm, 1.8 micron; Solvent A=0.1% TFA in water; Solvent B=0.1% TFA in ACN; gradient 0-100% B over 2 min; retention time: 0.79 min; LCMS (ES-API), m/z 526.9 (M+H).

Workup

  1. temperatureGradually, the reaction temperature was raised to room temperature
  2. additionDiluted the reaction mixture
  3. customquenched by addition of 5% citric acid solution
  4. extractionExtracted the reaction mixture in DCM
  5. customThe organic layer was collected
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude material was purified by column chromatography through silica gel and MeOH

Sources & evidence

ORD record
ord-1af5848d40f743ee81040c908b025090
Source dataset
uspto-grants-2015_03
Patent number
US08987311B2

Reaction notes

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