Diisopropylethylamine → 2-(2-Cyclobutoxy-5-hydroxymethyl-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester

HRID 1047896Notes

Reaction equation

HRID 1047896 reaction equation
[CH:1]1([O:5][C:6]2[C:14]([CH3:15])=[CH:13][C:12]([CH2:16][OH:17])=[CH:11][C:7]=2[C:8]([OH:10])=O)[CH2:4][CH2:3][CH2:2]1.[CH2:18]([O:20][C:21]([C:23]1([NH2:32])[CH2:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24]1)=[O:22])[CH3:19].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>[CH2:18]([O:20][C:21]([C:23]1([NH:32][C:8](=[O:10])[C:7]2[CH:11]=[C:12]([CH2:16][OH:17])[CH:13]=[C:14]([CH3:15])[C:6]=2[O:5][CH:1]2[CH2:2][CH2:3][CH2:4]2)[CH2:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24]1)=[O:22])[CH3:19]

Participants

7

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 593143012-Cyclobutoxy-5-hydroxymethyl-3-methyl-benzoic acid

Product 1

HCID 593141022-(2-Cyclobutoxy-5-hydroxymethyl-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl esterYield 10%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-cyclobutoxy-5-hydroxymethyl-3-methyl-benzoic acid (410 mg, 1.7 mmol), 2-amino-indan-2-carboxylic acid ethyl ester (425 mg, 1.7 mmol), HATU (760 mg, 2 mmol) in anhydrous DMF (5 mL) is added DIPEA (4354, 2.5 mmol). The resulting solution is stirred at RT overnight. Water (10 mL) is poured into the reaction mixture, and then extracted with EtOAc (3×7 mL). The combined organic layers are concentrated in vacuo. The residue is purified by reverse phase chromatography (gradient elution: 20-100% ACN in water) to give product (285) as colorless oil (70 mg, 10%).

Workup

  1. extractionextracted with EtOAc (3×7 mL)
  2. concentrationThe combined organic layers are concentrated in vacuo
  3. customThe residue is purified by reverse phase chromatography (gradient elution: 20-100% ACN in water)

Sources & evidence

ORD record
ord-4d9b20dc85db436e92f258bb34e08a92
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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