N,O-Dimethylhydroxylamine → 2-(4-(5-bromopyrimidin-2-ylamino)phenyl)-N-methoxy-N-methylacetamide

HRID 2067874Notes

Reaction equation

HRID 2067874 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=O)=[CH:11][CH:10]=2)=[N:6][CH:7]=1.CN([C:22]([O:26][N:27]1N=NC2C=CC=N[C:28]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CNOC.C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[N:6][C:5]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([CH2:15][C:16]([N:27]([O:26][CH3:22])[CH3:28])=[O:18])=[CH:13][CH:14]=2)=[N:4][CH:3]=1

Participants

7

Reactant 4

HCID 14232N,O-DimethylhydroxylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 687273072-(4-(5-Bromopyrimidin-2-ylamino)phenyl)acetic acid

Product 1

HCID 866601182-(4-(5-bromopyrimidin-2-ylamino)phenyl)-N-methoxy-N-methylacetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-(4-(5-Bromopyrimidin-2-ylamino)phenyl)acetic acid 22 (5.0 mmol) and HATU (6.0 mmol) are dissolved in dry DMF (10 mL) and stirred for 10 min. Then N,O-dimethylhydroxylamine (7.5 mmol) and diisopropylethylamine (15.0 mmol) are added to the solution. The reaction mixture is stirred for 1 h at rt. After the reaction is complete, the reaction mixture is added dropwise into water (100 mL). The precipitate is filtered and dried to yield 2-(4-(5-bromopyrimidin-2-ylamino)phenyl)-N-methoxy-N-methylacetamide 23. 1H NMR (400 MHz, d6-DMSO) δ 9.82 (s, 1H), 8.58 (s, 2H), 7.61 (d, J=8.4 Hz, 2H), 7.15 (d, J=8.4 Hz, 2H), 3.67 (s, 3H), 3.34 (s, 2H), 3.10 (s, 3H). MS (m/z) (M+1)+: 351.0, 353.0.

Workup

  1. stirringThe reaction mixture is stirred for 1 h at rt
  2. filtrationThe precipitate is filtered
  3. customdried

Sources & evidence

ORD record
ord-62b7cd42e3594fa78a33a3c9d7fecca3
Source dataset
uspto-grants-2012_10
Patent number
US08293757B2

Reaction notes

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