Diisopropylethylamine → HCID 59314291, compound

HRID 1047854Notes

Reaction equation

HRID 1047854 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].[C:16]([C:18]1[C:19]([CH3:27])=[C:20]([CH:24]=[CH:25][CH:26]=1)[C:21](O)=[O:22])#[N:17].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>>[CH2:1]([O:3][C:4]([C:6]1([NH:15][C:21](=[O:22])[C:20]2[CH:24]=[CH:25][CH:26]=[C:18]([C:16]#[N:17])[C:19]=2[CH3:27])[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 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 10921653Ethyl 2-amino-2,3-dihydro-1H-indene-2-carboxylateHCID 233592293-Cyano-2-methylbenzoic acid

Product 1

HCID 59314291HCID 59314291, compoundYield 89.2%

Procedure

2-Amino-indane-2-carboxylic acid ethyl ester (250 mg, 1.2 mmol), 3-cyano-2-methyl-benzoic acid (196 mg, 1.2 mmol) and HATU (555 mg, 1.46 mmol) are taken in a vial, evacuated and refilled with nitrogen. Anhydrous DMF (2 mL) is added and stirring is initiated. After a few min, DIPEA (0.302 mL, 1.82 mmol) is added and stirred at RT overnight. Analysis by tlc of the reaction mixture (silica, 50% EtOAc/heptanes) indicates complete consumption of the starting amine. Water (10 mL) is added, extracted with EtOAc (3×5 mL), dried over Na2SO4, concentrated and the crude product is chromatographed on a 25 g silica gel column using 20-50% EtOAc in heptane as a gradient to afford 2-(3-cyano-2-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (373 mg, 89%).

Workup

  1. customevacuated
  2. additionrefilled with nitrogen
  3. additionAnhydrous DMF (2 mL) is added
  4. stirringstirred at RT overnight
  5. customconsumption of the starting amine
  6. additionWater (10 mL) is added
  7. extractionextracted with EtOAc (3×5 mL)
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. customthe crude product is chromatographed on a 25 g silica gel column

Sources & evidence

ORD record
ord-c7df70b298c24ed287a463d7b537e854
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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