Diisopropylethylamine → HCID 59314389, compound

HRID 1047898Notes

Reaction equation

HRID 1047898 reaction equation
[CH:1]1([O:5][C:6]2[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:7]=2[C:8]([OH:10])=O)[CH2:4][CH2:3][CH2:2]1.[CH2:16]([O:18][C:19](=[O:31])[CH2:20][C:21]1([NH2:30])[CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22]1)[CH3:17].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH2:16]([O:18][C:19](=[O:31])[CH2:20][C:21]1([NH:30][C:8](=[O:10])[C:7]2[CH:11]=[CH:12][CH:13]=[C:14]([CH3:15])[C:6]=2[O:5][CH:1]2[CH2:2][CH2:3][CH2:4]2)[CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22]1)[CH3:17]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57443998Ethyl 2-amino-2,3-dihydro-1H-indene-2-acetateHCID 593141552-Cyclobutyloxy-3-methylbenzoic acid

Product 1

HCID 59314389HCID 59314389, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-cyclobutyloxy-3-methylbenzoic acid (210 mg-1.02 mmol), 2-aminoindan-2-acetic acid ethyl ester (A6) (260 mg-1.02 mmol) and HATU (470 mg-1.224 mmol-1.2 eq) in dry DMF (10 mL) is added diisopropylethylamine (0.36 mL-2.24 mmol-2.2 eq) and the resulting solution is stirred at RT overnight. After the removal of the DMF in vacuo, the residue is dissolved in EtOAc (60 mL) and washed with water (2×20 mL) and brine (2×20 mL). The organic layer is dried over MgSO4 and concentrated in vacuo. The residue is purified by flash chromatography (120 g silica gel, 15% EtOAc in heptane) to give the pure product as colorless oil (400 mg, 96%).

Workup

  1. customAfter the removal of the DMF in vacuo
  2. dissolutionthe residue is dissolved in EtOAc (60 mL)
  3. washwashed with water (2×20 mL) and brine (2×20 mL)
  4. dry with materialThe organic layer is dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by flash chromatography (120 g silica gel, 15% EtOAc in heptane)

Sources & evidence

ORD record
ord-9341780258de4a97a3faec159996e1ca
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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