Diisopropylethylamine → HCID 68505027, compound

HRID 2387238Notes

Reaction equation

HRID 2387238 reaction equation
[CH3:1][C:2]1[C:3]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([F:20])=[C:15]([CH:19]=2)[C:16]([OH:18])=O)=[N:4][NH:5][C:6](=[O:9])[C:7]=1[CH3:8].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[CH2:52]([O:54][CH:55]([O:63][CH2:64][CH3:65])[CH2:56][NH:57][CH2:58][C:59]([O:61][CH3:62])=[O:60])[CH3:53]>CN(C=O)C.CCOC(C)=O>[CH2:64]([O:63][CH:55]([O:54][CH2:52][CH3:53])[CH2:56][N:57]([C:16](=[O:18])[C:15]1[CH:19]=[C:11]([CH2:10][C:3]2[C:2]([CH3:1])=[C:7]([CH3:8])[C:6](=[O:9])[NH:5][N:4]=2)[CH:12]=[CH:13][C:14]=1[F:20])[CH2:58][C:59]([O:61][CH3:62])=[O:60])[CH3:65]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 59535479HCID 59535479, compoundHCID 68502767HCID 68502767, compound

Product 1

HCID 68505027HCID 68505027, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-[(4,5-dimethyl-6-oxo-1,6-dihydropyridazin-3-yl)methyl]-2-fluorobenzoic acid (Preparative Example 2) (1 eq), TBTU (1.2 eq), and DIPEA (1.5 eq) in DMF (0.18M) was added methyl N-(2,2-diethoxyethyl)glycinate (1 eq) (prepared as described in Synthesis 2002, 2, 242-252), and the mixture was stirred at RT for 2 h. The reaction was diluted with EtOAc, washed sequentially with 1N HCl, sat. aq. NaHCO3 solution, and then with brine. The organic layers were dried (Na2SO4), filtered and concentrated and concentrated under reduced pressure. MS (ES) C23H30FN3O6 required: 463, found: 464 (M+H)+; 486 (M+Na)+.

Workup

  1. washwashed sequentially with 1N HCl, sat. aq. NaHCO3 solution
  2. dry with materialThe organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5df8d61f715644c5992672d8523c4255
Source dataset
uspto-grants-2012_09
Patent number
US08268827B2

Reaction notes

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