Diisopropylethylamine → HCID 59314370, compound

HRID 1047868Notes

Reaction equation

HRID 1047868 reaction equation
[CH3:1][C:2]([C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=O)([CH3:5])[CH2:3][CH3:4].[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.O>[CH2:15]([O:17][C:18]([C:20]1([NH:29][C:8](=[O:10])[C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[C:2]([CH3:1])([CH3:5])[CH2:3][CH3:4])[CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21]1)=[O:19])[CH3:16]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 8167120HCID 8167120, compoundHCID 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 59314370HCID 59314370, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(1,1-dimethyl-propyl)-benzoic acid (140 mg, 0.73 mmol), 2-amino-indan-2-carboxylic acid ethyl ester (150 mg, 0.73 mmol), HATU (333 mg, 0.87 mmol) in anhydrous DMF (1 mL) is added DIPEA (1904, 1.1 mmol). The resulting solution is stirred at RT overnight. Water (10 mL) is then poured into the reaction mixture, and then the reaction mixture is extracted with EtOAc (3×5 mL). The combined organic layers are concentrated in vacuo. The residue is purified by flash column chromatography (12 g silica gel, gradient elution: 0-30% EtOAc in heptane) to give product (247) as yellow oil (220 mg, 89%).

Workup

  1. extractionthe reaction mixture is extracted with EtOAc (3×5 mL)
  2. concentrationThe combined organic layers are concentrated in vacuo
  3. customThe residue is purified by flash column chromatography (12 g silica gel, gradient elution: 0-30% EtOAc in heptane)

Sources & evidence

ORD record
ord-5cc59068cb54455397c66b283cd51f70
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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