Water → HCID 86713685, compound

HRID 1430552Notes

Reaction equation

HRID 1430552 reaction equation
[NH2:1][C:2]1[C:3]([F:23])=[CH:4][C:5]([Cl:22])=[C:6]([C:8]2[C:9](=[O:21])[N:10]([CH2:19][CH3:20])[C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[C:13](Cl)[CH:12]=3)[CH:7]=1.[OH2:24]>O1CCN(CCCN)CC1>[NH2:1][C:2]1[C:3]([F:23])=[CH:4][C:5]([Cl:22])=[C:6]([C:8]2[C:9](=[O:21])[N:10]([CH2:19][CH3:20])[C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[C:13]([NH:14][CH2:13][CH2:12][CH2:11][N:10]2[CH2:19][CH2:20][O:24][CH2:8][CH2:9]2)[CH:12]=3)[CH:7]=1

Participants

4

Reactant 2

HCID 962WaterHCID 877715763-(5-Amino-2-chloro-4-fluorophenyl)-7-chloro-1-ethyl-1,6-naphthyridin-2(1h)-one

Product 1

HCID 86713685HCID 86713685, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 61055N-(3-Aminopropyl)morpholineSolvent

Procedure

A suspension of Example A3 (0.200 g, 0.568 mmol) in 3-morpholinopropan-1-amine (1 mL) was subjected to microwave irradiation at 160° C. for 30 minutes. The mixture was cooled to RT, treated with water and the aqueous liquid decanted. The material was treated with MTBE and the resulting solid collected via filtration to afford 3-(5-amino-2-chloro-4-fluorophenyl)-1-ethyl-7-((3-morpholinopropyl)amino)-1,6-naphthyridin-2(1H)-one (150 mg, 57% yield). MS (ESI) m/z: 460.1 [M+H]+.

Workup

  1. customirradiation at 160° C. for 30 minutes
  2. customthe aqueous liquid decanted
  3. additionThe material was treated with MTBE
  4. filtrationthe resulting solid collected via filtration

Sources & evidence

ORD record
ord-57e0f020987f43b59159a2e3b5932f6c
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

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