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3-Chlorosalicylic acid → 2-(3-Chloro-2-hydroxy-benzoylamino)-indan-2-carboxylic acid ethyl ester

HRID 1047671
Notes
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Reaction equation

HRID 1047671 reaction equation
[Cl:1][C:2]1[C:3]([OH:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.[CH2:12]([O:14][C:15]([C:17]1([NH2:26])[CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18]1)=[O:16])[CH3:13].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>[CH2:12]([O:14][C:15]([C:17]1([NH:26][C:5](=[O:7])[C:4]2[CH:8]=[CH:9][CH:10]=[C:2]([Cl:1])[C:3]=2[OH:11])[CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18]1)=[O:16])[CH3:13]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 745853-Chlorosalicylic acidHCID 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-carboxylate

Product 1

HCID 593141222-(3-Chloro-2-hydroxy-benzoylamino)-indan-2-carboxylic acid ethyl ester
Yield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-chloro-2-hydroxy-benzoic acid (413 mg, 2.4 mmol), 2-Amino-indan-2-carboxylic acid ethyl ester (500 mg, 2.4 mmol), HATU (1.1 g, 2.9 mmol) in anhydrous DMF (10 mL) is added DIPEA (0.88 ml, 5.3 mmol). The resulting solution is stirred at RT overnight. After the removal of DMF in vacuo, the residue is dissolved in EtOAc (50 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: 10%-80% EtOAc in heptane) to give a pure product (14) as white solid (420 mg, 49%).

Workup

  1. customAfter the removal of DMF in vacuo
  2. dissolutionthe residue is dissolved in EtOAc (50 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: 10%-80% EtOAc in heptane)

Sources & evidence

ORD record
ord-11921af1372a41eeaa055021e81937f9
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08569535B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes