Bicyclo[2.2.1]heptane-2-carboxylic acid → HCID 59314273, compound

HRID 1047883Notes

Reaction equation

HRID 1047883 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[C:8]([OH:10])=O.[CH2:11]([O:13][C:14]([C:16]1([NH2:25])[CH2:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17]1)=[O:15])[CH3:12].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>[CH2:11]([O:13][C:14]([C:16]1([NH:25][C:8]([CH:2]2[CH2:3][CH:4]3[CH2:7][CH:1]2[CH2:6][CH2:5]3)=[O:10])[CH2:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17]1)=[O:15])[CH3:12]

Participants

7

Reactant 4

HCID 79113Bicyclo[2.2.1]heptane-2-carboxylic 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 59314273HCID 59314273, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of bicyclo[2.2.1]heptane-2-carboxylic acid (102 mg, 0.73 mmol), 2-amino-indan-2-carboxylic acid ethyl ester (150 mg, 0.73 mmol), HATU (333 mg, 0.87 mmol) in anhydrous DMF (1 mL) is added DIPEA (1904, 1.10 mmol). The resulting solution is stirred at RT overnight. Water (10 mL) is poured into the reaction mixture and then extracted with EtOAc (3×5 mL). The combined organic layers are concentrated in vacuo. The residue is purified by flash column chromatography (12 g silica gel, gradient elution: 0-30% EtOAc in heptane) to give product (272) as yellow oil (148 mg, 62%).

Workup

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

Sources & evidence

ORD record
ord-be635d60576b4ca4bc8d23a81825fac0
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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