Diisopropylethylamine → HCID 59314123, compound

HRID 1047881Notes

Reaction equation

HRID 1047881 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([NH2:15])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2].CN(C(ON1N=N[C:26]2[CH:27]=[CH:28][CH:29]=N[C:25]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN([CH:46]([CH3:48])[CH3:47])C(C)C>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1([NH:15][C:1](=[O:3])[CH:2]([CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29]2)[C:47]2[CH:46]=[CH:48][CH:7]=[CH:6][CH:4]=2)[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10921653Ethyl 2-amino-2,3-dihydro-1H-indene-2-carboxylate

Product 1

HCID 59314123HCID 59314123, compoundYield 161.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of α-phenylcyclopenteacetic acid (2.04 g, 10 mmol), 2-Amino-indan-2-carboxylic acid ethyl ester (2.05 g, 10 mmol), HATU (7.60 g, 20 mmol) in anhydrous DMF (50 mL) is added DIPEA (3.30 mL, 20 mmol). The resulting solution is stirred at RT overnight. After the removal of DMF in vacuo, the residue is dissolved in EtOAc (100 mL) and washed with saturated NaHCO3 (1×100 mL), water (1×100 mL) and brine (1×100 mL). The organic layer is dried over anhydrous Na2SO4 and concentrated in vacuo. The residue is purified by flash column chromatography (115 g silica gel, gradient elution: 0%-20% EtOAc in heptane) to give a pure product (268) as a solid (3.16 g, 82%).

Workup

  1. customAfter the removal of DMF in vacuo
  2. dissolutionthe residue is dissolved in EtOAc (100 mL)
  3. washwashed with saturated NaHCO3 (1×100 mL), water (1×100 mL) and brine (1×100 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 (115 g silica gel, gradient elution: 0%-20% EtOAc in heptane)

Sources & evidence

ORD record
ord-847aa4174277498f9ce13a804e3738dc
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

Loading…