Citric Acid → HCID 58147649, compound

HRID 1944122Notes

Reaction equation

HRID 1944122 reaction equation
CN(C(ON1N=N[C:11]2[CH:12]=[CH:13][CH:14]=N[C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:25]([O:29][C:30]([N:32]1[CH2:38][CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26].CCN(C(C)C)C(C)C.C(O)(=O)C[C:50](CC(O)=O)(C(O)=O)[OH:51]>ClCCl>[C:25]([O:29][C:30]([N:32]1[CH2:38][CH2:37][CH2:36][N:35]([C:50]([C:11]2([CH3:10])[CH2:12][CH2:13][CH2:14]2)=[O:51])[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:26])[CH3:27]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 81531DiisopropylethylamineHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 58147649HCID 58147649, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

HATU (1.71 g), [1,4]diazepane-1-carboxylic acid tert-butyl ester (0.813 ml) and DIPEA (3.58 ml) were added to a solution of the product of example 104b (470 mg) in dichloromethane (20 ml). After stirring for 2 h at room temperature, the reaction mixture was poured in an aqueous citric acid solution (10%) and extracted with ethyl acetate. The organic layer was washed with a sat. aqueous NaHCO3 solution, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by chromatography on silica in toluene/acetone [100/0→3/1 (v/v)] as eluent.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with a sat. aqueous NaHCO3 solution
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography on silica in toluene/acetone [100/0→3/1 (v/v)] as eluent

Sources & evidence

ORD record
ord-0578fcd9418140baaf89c27f395e1bfc
Source dataset
uspto-grants-2013_03
Patent number
US08394789B2

Reaction notes

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