Toluene → HCID 57457834, compound

HRID 1363621Notes

Reaction equation

HRID 1363621 reaction equation
[NH2:1][C:2]1[CH2:3][N:4](NCC2(O)CCCC2)[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.C([O:27][CH2:28][CH3:29])(OCC)OCC.Cl.[N:31]1[CH:36]=CC=C[CH:32]=1.[C:37]1(C)[CH:42]=CC=C[CH:38]=1>>[N:31]1([CH2:36][C:28]2([OH:27])[CH2:29][CH2:42][CH2:37][CH2:38]2)[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=[CH:32]1

Participants

5

Reactant 4

HCID 1140TolueneHCID 31214Ethyl orthoformateHCID 10176127Pyridinium chlorideHCID 66919169HCID 66919169, compound

Product 1

HCID 57457834HCID 57457834, compound

Procedure

A mixture of 1-{{(3-aminoquinolin-1-yl)amino]methyl}cyclopentanol (2.00 g, 7.8 mmol, Example 3 Parts A through D), triethyl orthoformate (1.36 mL, 8.2 mmol), pyridine hydrochloride (0.2 g), and toluene (20 mL) was heated at reflux for 3.5 hours. The reaction mixture was allowed to cool to ambient temperature. A solid was isolated by filtration and dried. The solid was triturated with a minimum amount of saturated aqueous sodium bicarbonate for 1 hour. The solid was filtered and then dried to provide 1.85 g of 1-[(1H-imidazo[4,5-c]quinolin-1-yl)methyl]cyclopentanol as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3.5 hours
  3. customA solid was isolated by filtration
  4. customdried
  5. customThe solid was triturated with a minimum amount of saturated aqueous sodium bicarbonate for 1 hour
  6. filtrationThe solid was filtered
  7. customdried

Sources & evidence

ORD record
ord-d06588dc04fe4626ba631a2712008865
Source dataset
uspto-grants-2011_02
Patent number
US07884207B2

Reaction notes

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