N-(3-Aminopropyl)morpholine → HCID 67272396, compound

HRID 600252Notes

Reaction equation

HRID 600252 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[CH:11][C:12]([NH:14][C:15]2[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=2)[C:18]([OH:20])=O)=[O:13])=[CH:2]1.[N:24]1([CH2:30][CH2:31][CH2:32][NH2:33])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[Na]>CN(C)C=O.C(OCC)(=O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[CH:11][C:12]([NH:14][C:15]2[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=2)[C:18]([NH:33][CH2:32][CH2:31][CH2:30][N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[O:20])=[O:13])=[CH:2]1

Participants

8

Reactant 5

HCID 61055N-(3-Aminopropyl)morpholineHCID 81531DiisopropylethylamineHCID 5360545SodiumHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67273232HCID 67273232, compound

Product 1

HCID 67272396HCID 67272396, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 5.0 mL of dimethylformamide were dissolved 3-(3-1H-indol-3-yl-acryloylamino)-benzoic acid (150 mg, 0.49 mmol), prepared in Example 3, and 3-morpholin-4-yl-propylamine (0.11 mL, 0.73 mmol), followed by the addition of O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyl uronium hexafluorophosphate (277.6 mg, 0.73 mmol) and N,N-diisopropylethylamine (0.13 ml, 0.73 mmol). The resulting solution was stirred at room temperature and mixed with ethyl acetate and an aqueous sodium salt solution. The organic layer was dried over anhydrous magnesium sulfate. After the filtration and concentration of the residue, the concentrate was purified using Prep-TLC (methylene chloride:methanol=10:1) to produce the subject compound as a yellow solid (8) (92.6 mg, 44%).

Workup

  1. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  2. filtrationAfter the filtration and concentration of the residue
  3. customthe concentrate was purified

Sources & evidence

ORD record
ord-abeac2c6615745afaee6587f138554fd
Source dataset
uspto-grants-2011_03
Patent number
US07902190B2

Reaction notes

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