Morpholine → HCID 58539146, compound

HRID 2406316Notes

Reaction equation

HRID 2406316 reaction equation
[F:1][C:2]1[C:3]([NH:20][CH3:21])=[N:4][C:5]([NH:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][C:10]=2[O:18][CH3:19])=[N:6][CH:7]=1.[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C)C=O.CCOC(C)=O>[F:1][C:2]1[C:3]([NH:20][CH3:21])=[N:4][C:5]([NH:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[O:15])=[CH:11][C:10]=2[O:18][CH3:19])=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58539164HCID 58539164, compound

Product 1

HCID 58539146HCID 58539146, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 100 mg 4-(5-fluoro-4-(methylamino)pyrimidin-2-ylamino)-3-methoxybenzoic acid, 47 μL morpholine, 205 mg HATU, 188 mL diisopropylethylamine in 1 mL of dimethylformamide was stirred at room temperature overnight. The reaction was checked by LCMS and found to be complete. The reaction was diluted with EtOAc, and the organic layer washed with saturated NaHCO3 and brine. The organic layer was concentrated and purified by preparative reverse phase HPLC to yield 12 mg of (4-(5-fluoro-4-(methylamino)pyrimidin-2-ylamino)-3-methoxyphenyl)(morpholino)methanone.

Workup

  1. washthe organic layer washed with saturated NaHCO3 and brine
  2. concentrationThe organic layer was concentrated
  3. custompurified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-0e922e66d80e41fd8d0cbc4ba49fc99d
Source dataset
uspto-grants-2014_08
Patent number
US08809331B2

Reaction notes

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