4-Azaindole → HCID 58387946, compound

HRID 2080228Notes

Reaction equation

HRID 2080228 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=O)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C1(N=C=NC2CCCCC2)CCCCC1.[CH2:29]([O:36][C:37]1[CH:44]=[CH:43][C:40]([CH2:41][NH2:42])=[CH:39][CH:38]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.N1C2C(=NC=CC=2)C=C1>O1CCCC1>[CH2:29]([O:36][C:37]1[CH:38]=[CH:39][C:40]([CH2:41][NH:42][C:11]([C:7]2[CH:6]=[C:5]3[C:10](=[CH:9][CH:8]=2)[N:1]=[CH:2][CH:3]=[CH:4]3)=[O:13])=[CH:43][CH:44]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 92264-AzaindoleHCID 10868DicyclohexylcarbodiimideHCID 825716-Quinolinecarboxylic acidHCID 42928454-Benzyloxybenzylamine

Product 1

HCID 58387946HCID 58387946, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 6-quinoline carboxylic acid (100 mg, 0.577 mmol) in tetrahydrofuran (50 mL) was added N,N′-dicyclohexylcarbodiimide (1.90 g, 11.7 mmol), and the solution was stirred at room temperature for 1 hour. Then, to this solution was added a solution of 4-benzyloxybenzylamine described in Preparation Example 1 (2.49 g, 11.7 mmol) in tetrahydrofuran (5 mL), and the solution was stirred overnight at room temperature. The solvent was evaporated, the residue was purified by NH silica gel column chromatography (hexane:ethyl acetate), and the title compound (4.31 g, quantitatively) was obtained as a white solid.

Workup

  1. stirringthe solution was stirred overnight at room temperature
  2. customThe solvent was evaporated
  3. customthe residue was purified by NH silica gel column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-57afa207a71b46dcbdd0528f259402a8
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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