N-(3-Aminopropyl)morpholine → HCID 71293629, compound

HRID 1402556Notes

Reaction equation

HRID 1402556 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([C:13]3[NH:17][CH:16]=[C:15]([C:18](O)=[O:19])[CH:14]=3)[CH:8]=2)=[CH:4][C:3]=1[NH:23][C:24]([C:26]1[O:27][CH:28]=[CH:29][C:30]=1[CH3:31])=[O:25].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[O:65]1[CH2:70][CH2:69][N:68]([CH2:71][CH2:72][CH2:73][NH2:74])[CH2:67][CH2:66]1>CN(C=O)C.O>[F:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([C:13]3[NH:17][CH:16]=[C:15]([C:18]([NH:74][CH2:73][CH2:72][CH2:71][N:68]4[CH2:69][CH2:70][O:65][CH2:66][CH2:67]4)=[O:19])[CH:14]=3)[CH:8]=2)=[CH:4][C:3]=1[NH:23][C:24]([C:26]1[O:27][CH:28]=[CH:29][C:30]=1[CH3:31])=[O:25]

Participants

7

Reactant 4

HCID 61055N-(3-Aminopropyl)morpholineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 51001711HCID 51001711, compound

Product 1

HCID 71293629HCID 71293629, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 5-(4-{4-fluoro-3-[(3-methyl-2-furoyl)amino]phenoxy}pyridin-2-yl)-1H-pyrrole-3-carboxylic acid (Example 28) (150 mg, 0.36 mmol) in 10 ml of anhydrous DMF were added HATU (163 mg, 0.43 mmol) and N,N-diisopropylethylamine (102 mg, 0.79 mmol). The mixture was stirred at room temperature for 10 minutes, followed by addition of 3-morpholinopropylamine (104 mg, 0.72 mmol). The mixture was stirred for another 10 minutes and poured into 100 ml of water. The precipitates were filtered, washed with water and dried in vacuo to give the crude, which was purified by silica gel chromatography eluting with 10% methanol in chloroform to give 5-(4-{4-fluoro-3-[(3-methyl-2-furoyl)amino]phenoxy}pyridin-2-yl)-N-(3-morpholin-4-ylpropyl)-1H-pyrrole-3-carboxamide as white solid. Yield: 110 mg, 56%.

Workup

  1. stirringThe mixture was stirred for another 10 minutes
  2. filtrationThe precipitates were filtered
  3. washwashed with water
  4. customdried in vacuo
  5. customto give the crude, which
  6. customwas purified by silica gel chromatography
  7. washeluting with 10% methanol in chloroform

Sources & evidence

ORD record
ord-0f892519744343ddbc9ca9c6eb511da9
Source dataset
uspto-grants-2014_12
Patent number
US08906944B2

Reaction notes

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