6-Aminonicotinic acid → (6-Aminopyridin-3-yl)((3S,5S)-3,5-dimethylmorpholino)methanone

HRID 593145Notes

Reaction equation

HRID 593145 reaction equation
[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][C@H:4]([CH3:8])[NH:3]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:42][C:43]1[CH:51]=[CH:50][C:46]([C:47](O)=[O:48])=[CH:45][N:44]=1>CN(C=O)C>[NH2:42][C:43]1[N:44]=[CH:45][C:46]([C:47]([N:3]2[C@@H:4]([CH3:8])[CH2:5][O:6][CH2:7][C@@H:2]2[CH3:1])=[O:48])=[CH:50][CH:51]=1

Participants

6

Reactant 4

HCID 184966-Aminonicotinic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11768549(3S,5S)-3,5-Dimethylmorpholine

Product 1

HCID 86684581(6-Aminopyridin-3-yl)((3S,5S)-3,5-dimethylmorpholino)methanoneYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (3S,5S)-3,5-dimethylmorpholine (115 mg, 1.0 mmol) in DMF (2 mL) was added HATU (380 mg, 1.0 mmol), DIPEA (260 mg, 2.0 mmol), and 6-aminonicotinic acid (138 mg, 1.0 mmol) at room temperature. After stirring for 18 h, the reaction mixture was filtered and purified with Combiflash (A: 1% NH4HCO3/water, B: acetonitrile) to afford 324a (80 mg, 34%) as a yellow solid. MS (ESI): 236.1 (M+H).

Workup

  1. filtrationthe reaction mixture was filtered
  2. custompurified with Combiflash (A: 1% NH4HCO3/water, B

Sources & evidence

ORD record
ord-525cef30630d48788f29ee2ee355a5d2
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

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