Dimethylhydroxylamine → HCID 71622478, compound

HRID 2174248Notes

Reaction equation

HRID 2174248 reaction equation
[NH:1]([C:8]1[CH:13]=[C:12]([NH:14][C:15](=[O:19])[NH:16][CH2:17][CH3:18])[N:11]=[CH:10][C:9]=1[C:20]([NH:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31]([OH:33])=O)=[CH:25][CH:24]=1)=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)O.CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.CN([C:57](=[N+](C)C)[O:58][N:59]1[C:63]2=NC=CC=C2N=N1)C>CN(C=O)C.CCOC(C)=O>[CH2:17]([NH:16][C:15](=[O:19])[NH:14][C:12]1[CH:13]=[C:8]([NH:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9]([C:20]([NH:22][C:23]2[CH:24]=[CH:25][C:26]([CH2:29][CH2:30][C:31]([N:59]([O:58][CH3:57])[CH3:63])=[O:33])=[CH:27][CH:28]=2)=[O:21])=[CH:10][N:11]=1)[CH3:18]

Participants

7

Reactant 4

HCID 27970DimethylhydroxylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 71621798HCID 71621798, compound2×

Product 1

HCID 71622478HCID 71622478, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-[4-[[4-anilino-6-(ethylcarbamoylamino)pyridine-3-carbonyl]amino]phenyl]propanoic acid (Compound 78) (14.5 mg, 0.032 mmol) and dimethyl hydroxylamine (3.8 mg, 0.039 mmol) were dissolved in DMF (1 mL) and the DIPEA (17 μL, 0.098 mmol) added, followed by [dimethylamino(triazolo[4,5-b]pyridin-3-yloxy)methylene]-dimethyl-ammonium hexafluorophosphate (15 mg, 0.039 mmol). The mixture was stirred at RT. After 1 h the mixture was diluted with EtOAc and evaporated to dryness. The residue was dissolved in DCM and applied to a silica column, eluting with MeOH/DCM, to afford Compound 123 (8 mg).

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in DCM
  3. washeluting with MeOH/DCM

Sources & evidence

ORD record
ord-83703abc24f14c4cb162b926dd893b88
Source dataset
uspto-grants-2015_06
Patent number
US09060515B2

Reaction notes

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