Diisopropylethylamine → 2-(2-Isobutyryl-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester

HRID 1047848Notes

Reaction equation

HRID 1047848 reaction equation
[C:1]([C:6]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=O)(=[O:5])[CH:2]([CH3:4])[CH3:3].[CH2:16]([O:18][C:19]([C:21]1([NH2:30])[CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22]1)=[O:20])[CH3:17].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>CN(C=O)C>[CH2:16]([O:18][C:19]([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[C:1](=[O:5])[CH:2]([CH3:3])[CH3:4])[CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22]1)=[O:20])[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 10921653Ethyl 2-amino-2,3-dihydro-1H-indene-2-carboxylateHCID 593141812-Isobutyryl-3-methyl-benzoic acid

Product 1

HCID 593142722-(2-Isobutyryl-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl esterYield 89.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-isobutyryl-3-methyl-benzoic acid (227) (200 mg, 0.97 mmol), 2-amino-indan-2-carboxylic acid ethyl ester (220 mg, 1.07 mmol), HATU (441 mg, 1.16 mmol) in anhydrous DMF (10 mL) is added DIPEA (192 μL, 1.16 mmol). The resulting solution is stirred at RT overnight. After the removal of DMF in vacuo, the residue is dissolved in DCM (50 mL) and washed with water (1×5 mL) and brine (1×5 mL). The organic layer is dried over anhydrous Na2SO4 and concentrated in vacuo. The residue is purified by HPLC to give a pure product (228) as a pale yellow solid (340 mg, 89%).

Workup

  1. customAfter the removal of DMF in vacuo
  2. dissolutionthe residue is dissolved in DCM (50 mL)
  3. washwashed with water (1×5 mL) and brine (1×5 mL)
  4. dry with materialThe organic layer is dried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by HPLC

Sources & evidence

ORD record
ord-1845e479517e4873bf29498329093dfe
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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