Triethylamine → 4-(2,3-dihydro-2-oxo-1H-imidazo[4,5-b]quinolin-7-yloxy)-N-[1-(phenylmethyl)-4-piperidinyl]butanamide

HRID 2166023Notes

Reaction equation

HRID 2166023 reaction equation
[O:1]=[C:2]1[NH:21][C:5]2=[N:6][C:7]3[CH:8]=[CH:9][C:10]([O:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=O)=[CH:11][C:12]=3[CH:13]=[C:4]2[NH:3]1.[NH2:22][CH:23]1[CH2:28][CH2:27][N:26]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:25][CH2:24]1.C(N(CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>CN(C)C1C=CN=CC=1.O.CN(C)C=O>[O:1]=[C:2]1[NH:21][C:5]2=[N:6][C:7]3[CH:8]=[CH:9][C:10]([O:14][CH2:15][CH2:16][CH2:17][C:18]([NH:22][CH:23]4[CH2:28][CH2:27][N:26]([CH2:29][C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[CH2:25][CH2:24]4)=[O:20])=[CH:11][C:12]=3[CH:13]=[C:4]2[NH:3]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 4158521-Benzyl-4-piperidylamineHCID 142809904-(2-Oxo-2,3-dihydro-1H-imidazo[4,5-b]quinolin-7-yloxy)-butyric acid

Product 1

HCID 150056464-(2,3-dihydro-2-oxo-1H-imidazo[4,5-b]quinolin-7-yloxy)-N-[1-(phenylmethyl)-4-piperidinyl]butanamide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-[(2,3-dihydro-2-oxo-1H-imidazo-[4,5-b]quinolin-7-yl)oxy]butyric acid (2 g, 7mmol), 4-amino-1-benzylpiperidine (1.59 g, 1.70 mL, 8.4 mmol), triethylamine (1.54 g, 2.12 mL, 15.2 mmol), diphenylphosphoryl azide (2.87 g, 2.25 mL, 10.4 mmol), 4-dimethylaminopyridine (catalytic quantity) and dimethylformamide (40 mL) was stirred at room temperature for 18 hours. The mixture was then diluted with water and the crude free base product collected. After air drying, the free base was suspended in methanol and acidified with a 10% solution of hydrogen chloride in ethanol. The solution was evaporated and the residue dissolved in methanol. Dilution of the methanol solution with diethyl ether gave 4-(2,3-dihydro-2-oxo-1H-imidazo[4,5-b]quinolin-7-yloxy)-N-[1-(phenylmethyl)-4-piperidinyl]butanamide as the hydrated dihydrochloride salt (3.00 g, 80%), mp. 202°-204 C.

Workup

  1. customthe crude free base product collected
  2. customAfter air drying
  3. customThe solution was evaporated
  4. dissolutionthe residue dissolved in methanol

Sources & evidence

ORD record
ord-ae8b87762a98414a99de249d4fd930e0
Source dataset
uspto-grants-1990_07
Patent number
US04943573

Reaction notes

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