2-Methoxyethylamine → HCID 57690922, compound

HRID 219133Notes

Reaction equation

HRID 219133 reaction equation
C(N(C(C)C)C(C)C)C.Cl.[F:11][C:12]1[CH:20]=[C:19]([C:21]2[CH:22]=[CH:23][C:24]3[N:25]([C:27]([CH2:30][O:31][C:32]4[C:41]5[C:36](=[CH:37][C:38]([O:42][CH3:43])=[CH:39][CH:40]=5)[N:35]=[CH:34][CH:33]=4)=[N:28][N:29]=3)[CH:26]=2)[CH:18]=[CH:17][C:13]=1[C:14](Cl)=[O:15].[CH3:44][O:45][CH2:46][CH2:47][NH2:48]>C(Cl)Cl>[F:11][C:12]1[CH:20]=[C:19]([C:21]2[CH:22]=[CH:23][C:24]3[N:25]([C:27]([CH2:30][O:31][C:32]4[C:41]5[C:36](=[CH:37][C:38]([O:42][CH3:43])=[CH:39][CH:40]=5)[N:35]=[CH:34][CH:33]=4)=[N:28][N:29]=3)[CH:26]=2)[CH:18]=[CH:17][C:13]=1[C:14]([NH:48][CH2:47][CH2:46][O:45][CH3:44])=[O:15]

Participants

5

Reactant 3

HCID 80182-MethoxyethylamineHCID 81531DiisopropylethylamineHCID 86761581HCID 86761581, compound

Product 1

HCID 57690922HCID 57690922, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-ethyl-N-isopropylpropan-2-amine (0.077 ml, 0.44 mmol) and 2-fluoro-4-(3-((7-methoxyquinolin-4-yloxy)methyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)benzoyl chloride-HCl (0.088 g, 0.18 mmol) in DCM (1.25 mL) was added 2-methoxyethanamine (0.023 ml, 0.26 mmol) dropwise. The solution was stirred at room temperature for 5 h. The crude material was concentrated and then triturated with sodium bicarbonate and washed with water. The resultant solid was dissolved in DCM/MeOH and concentrated. The crude material was dissolved in DCM/MeOH and was purified via flash chromatography, eluting with 0-10% MeOH/NH4OH in DCM to yield 2-fluoro-N-(2-methoxyethyl)-4-(3-((7-methoxyquinolin-4-yloxy)methyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)benzamide.

Workup

  1. concentrationThe crude material was concentrated
  2. customtriturated with sodium bicarbonate
  3. washwashed with water
  4. dissolutionThe resultant solid was dissolved in DCM/MeOH
  5. concentrationconcentrated
  6. dissolutionThe crude material was dissolved in DCM/MeOH
  7. customwas purified via flash chromatography
  8. washeluting with 0-10% MeOH/NH4OH in DCM

Sources & evidence

ORD record
ord-0d5eb7e976394052b616102b9485a43b
Source dataset
uspto-grants-2012_06
Patent number
US08198448B2

Reaction notes

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