Diisopropylethylamine → HCID 136344049, compound

HRID 2037357Notes

Reaction equation

HRID 2037357 reaction equation
[CH2:1]([C:5]1[CH:10]=[C:9]([CH3:11])[N:8]=[C:7]([C:12]([OH:14])=O)[CH:6]=1)[CH:2]([CH3:4])[CH3:3].CCN(C(C)C)C(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[CH2:57]([C:59]1[CH:60]=[C:61]([CH:66]=[C:67]([CH3:70])[C:68]=1[OH:69])[C:62]([NH:64]O)=[NH:63])[CH3:58]>CN(C=O)C.O1CCOCC1>[CH2:57]([C:59]1[CH:60]=[C:61]([C:62]2[N:64]=[C:12]([C:7]3[CH:6]=[C:5]([CH2:1][CH:2]([CH3:3])[CH3:4])[CH:10]=[C:9]([CH3:11])[N:8]=3)[O:14][N:63]=2)[CH:66]=[C:67]([CH3:70])[C:68]=1[OH:69])[CH3:58]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 58418003HCID 58418003, compoundHCID 178436626HCID 178436626, compound

Product 1

HCID 136344049HCID 136344049, compoundYield 15.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-isobutyl-6-methyl-pyridine-2-carboxylic acid (480 mg, 2.09 mmol) and DIPEA (810 mg, 6.27 mmol) in DMF (20 mL), PyBOP (1150 mg, 2.21 mmol) is added at 0° C. The mixture is stirred for 15 min at 0° C. before 3-ethyl-4,N-dihydroxy-5-methyl-benzamidine (429 mg, 2.21 mmol) is added and stirring is continued for 1 h at 0° C. The reaction is quenched by adding water, the mixture is diluted with sat. aq. NaHCO3-solution and extracted twice with EA. The combined org. extracts are dried over MgSO4, filtered and concentrated to give the crude hydroxy-amidine ester intermediate; LC-MS: tR=0.90 min, [M+H]+=370.16. This material is dissolved in dioxane (10 mL) and the mixture is stirred at 80° C. for 15 h. The solvent is evaporated and the crude product is purified by CC on silica gel eluting with heptane:EA 7:3 to give the title compound (112 mg) as a pale purple oil; LC-MS: tR=1.12 min, [M+H]+=352.17.

Workup

  1. additionis added
  2. customThe reaction is quenched
  3. additionby adding water
  4. additionthe mixture is diluted with sat. aq. NaHCO3-solution
  5. extractionextracted twice with EA
  6. dry with materialextracts are dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give the crude hydroxy-amidine ester intermediate
  10. stirringthe mixture is stirred at 80° C. for 15 h
  11. customThe solvent is evaporated
  12. customthe crude product is purified by CC on silica gel eluting with heptane:EA 7:3

Sources & evidence

ORD record
ord-ee98fffba2bb4f24b2a038c97334f67c
Source dataset
uspto-grants-2013_11
Patent number
US08575200B2

Reaction notes

Loading…