Diisopropylethylamine → HCID 59314311, compound

HRID 1047796Notes

Reaction equation

HRID 1047796 reaction equation
[I:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH2:12]([O:14][C:15]([C:17]1([NH2:28])[CH2:25][C:24]2[C:19](=[CH:20][C:21]([F:27])=[C:22]([F:26])[CH:23]=2)[CH2:18]1)=[O:16])[CH3:13].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:12]([O:14][C:15]([C:17]1([NH:28][C:4](=[O:6])[C:3]2[CH:7]=[CH:8][CH:9]=[C:10]([CH3:11])[C:2]=2[I:1])[CH2:25][C:24]2[C:19](=[CH:20][C:21]([F:27])=[C:22]([F:26])[CH:23]=2)[CH2:18]1)=[O:16])[CH3:13]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27593652-Iodo-3-methylbenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 39977428HCID 39977428, compound

Product 1

HCID 59314311HCID 59314311, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-iodo-3-methyl-benzoic acid (1.50 g, 5.75 mmol), 2-amino-5,6-difluoro-indan-2-carboxylic acid ethyl ester (1.39 g, 5.75 mmol), HATU (2.63 g, 6.90 mmol) in anhydrous DMF (6 mL) is added DIPEA (1.14 mL, 6.90 mmol). The resulting solution is stirred at RT overnight. After the removal of DMF in vacuo, the residue is dissolved in EtOAc (200 mL) and washed with water (1×20 mL) and brine (2×20 mL). The organic layer is dried over anhydrous Na2SO4 and concentrated in vacuo. The residue is purified by flash column chromatography (400 g silica gel, gradient elution: 10%-80% EtOAc in heptane) to give a pure product (156) as white solid (2.32 g, 83%).

Workup

  1. customAfter the removal of DMF in vacuo
  2. dissolutionthe residue is dissolved in EtOAc (200 mL)
  3. washwashed with water (1×20 mL) and brine (2×20 mL)
  4. dry with materialThe organic layer is dried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by flash column chromatography (400 g silica gel, gradient elution: 10%-80% EtOAc in heptane)

Sources & evidence

ORD record
ord-bb3e61b382a442a08673d6e827210bf8
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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