Diisopropylethylamine → HCID 59314387, compound

HRID 1047720Notes

Reaction equation

HRID 1047720 reaction equation
[O:1]=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[C:7]([C:12]([OH:14])=O)=[CH:6][CH:5]=[CH:4][C:3]1=2.[CH2:15]([O:17][C:18]([C:20]1([NH2:29])[CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21]1)=[O:19])[CH3:16].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>[CH2:15]([O:17][C:18]([C:20]1([NH:29][C:12]([C:7]2[C:8]3[CH2:9][CH2:10][CH2:11][C:2](=[O:1])[C:3]=3[CH:4]=[CH:5][CH:6]=2)=[O:14])[CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21]1)=[O:19])[CH3:16]

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 103976385-Oxo-5,6,7,8-tetrahydro-naphthalene-1-carboxylic acidHCID 10921653Ethyl 2-amino-2,3-dihydro-1H-indene-2-carboxylate

Product 1

HCID 59314387HCID 59314387, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-oxo-5,6,7,8-tetrahydro-naphthalene-1-carboxylic acid (430 mg, 2.26 mmol), 2-amino-indan-2-carboxylic acid ethyl ester (464 mg, 2.26 mmol), HATU (1 g, 2.70 mmol) in anhydrous DMF (20 mL) is added DIPEA (446 μL, 2.70 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 water (1×10 mL) and brine (2×10 mL). The organic layer is dried over anhydrous Na2SO4 and concentrated in vacuo. The residue is purified by flash column chromatography (120 g silica gel, gradient elution: 5-50% EtOAc in heptane) to give a pure product (65) as white solid (828 mg, 97%).

Workup

  1. customAfter the removal of DMF in vacuo
  2. dissolutionthe residue is dissolved in EtOAc (100 mL)
  3. washwashed with water (1×10 mL) and brine (2×10 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 (120 g silica gel, gradient elution: 5-50% EtOAc in heptane)

Sources & evidence

ORD record
ord-89cdd65be8d34e6797d0f352351502c9
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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