Dimethylamine → Dimethyl-{3-[4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-yloxy]-propyl}-amine

HRID 8249

Reaction equation

HRID 8249 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([C:16]3[C:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=4)=[N:19][N:18]4[CH2:27][CH2:28][CH2:29][C:17]=34)=[CH:11][CH:12]=[N:13]2)=[CH:8][CH:7]=1.[I-].[Na+].[CH3:32][NH:33][CH3:34].O1CCCC1>CN(C)C=O>[CH3:32][N:33]([CH3:34])[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([C:16]3[C:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=4)=[N:19][N:18]4[CH2:27][CH2:28][CH2:29][C:17]=34)=[CH:11][CH:12]=[N:13]2)=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 5238Sodium IodideHCID 8028TetrahydrofuranHCID 219925637-(3-Chloro-propoxy)-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline

Product 1

HCID 10112407Dimethyl-{3-[4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-yloxy]-propyl}-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 7-(3-chloro-propoxy)-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline (54 mg, 0.13 mmol), sodium iodide (5 mg, 0.03 mmol), and 2 N dimethylamine in tetrahydrofuran (3 mL, 6 mmol) in N,N-dimethylformamide (5 mL) is heated at 100° C. for 48 h. The mixture is cooled and concentrated in vacuo. The residue is chromatographed on SiO2 (100% ethyl acetate to 10% methanol in ethyl acetate) to yield the title compound, 41 mg (74%), as a brown solid.

Workup

  1. temperatureThe mixture is cooled
  2. concentrationconcentrated in vacuo
  3. customThe residue is chromatographed on SiO2 (100% ethyl acetate to 10% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-2037d4dea16e4b4ca6ee4112e129ee14
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Linked notes

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