o-Phenylbenzoic acid → HCID 86641474, compound

HRID 1047866Notes

Reaction equation

HRID 1047866 reaction equation
[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:2]([C:7]([OH:9])=O)=[CH:3][CH:4]=[CH:5][CH:6]=1.[CH2:16]([O:18][C:19]([C:21]1(N)[CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22]1)=[O:20])[CH3:17].C[N:32](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>[CH2:16]([O:18][C:19]([CH:21]1[CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]1[NH:32][C:7]([C:2]1[C:1]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:9])=[O:20])[CH3:17]

Participants

7

Reactant 4

HCID 70357o-Phenylbenzoic 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 86641474HCID 86641474, compoundYield 93.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of biphenyl-2-carboxylic acid (289 mg, 1.46 mmol), 2-amino-indan-2-carboxylic acid ethyl ester (300 mg, 1.46 mmol), HATU (666 mg, 1.75 mmol) in anhydrous DMF (1.8 mL) is added DIPEA (3814, 2.19 mmol). The resulting solution is stirred at RT overnight. Poured reaction into water (10 mL) and extracted with EtOAc (3×5 mL). The combined organic layers are concentrated in vacuo and the residue purified by flash column chromatography (12 g silica gel, gradient elution: 0-30% EtOAc in heptane) to give product (245) as off-white solid (525 mg, 93%).

Workup

  1. additionPoured
  2. extractionextracted with EtOAc (3×5 mL)
  3. concentrationThe combined organic layers are concentrated in vacuo
  4. customthe residue purified by flash column chromatography (12 g silica gel, gradient elution: 0-30% EtOAc in heptane)

Sources & evidence

ORD record
ord-fde830cb946a4bf4b9f757a0d856a199
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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