Diisopropylethylamine → HCID 178502896, compound

HRID 2202744Notes

Reaction equation

HRID 2202744 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:41])[C:7]=1[CH:8]([OH:40])[CH2:9][N:10]([CH2:31][C:32]1[CH:37]=[C:36]([F:38])[CH:35]=[C:34]([F:39])[CH:33]=1)[C:11]([C:13]1[CH:14]=[N:15][N:16]([C@H:22]2[CH2:27][CH2:26][C@H:25]([C:28]([OH:30])=O)[CH2:24][CH2:23]2)[C:17]=1[C:18]([F:21])([F:20])[F:19])=[O:12].Cl.[CH3:43][O:44][NH2:45].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>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:41])[C:7]=1[CH:8]([OH:40])[CH2:9][N:10]([CH2:31][C:32]1[CH:33]=[C:34]([F:39])[CH:35]=[C:36]([F:38])[CH:37]=1)[C:11]([C:13]1[CH:14]=[N:15][N:16]([C@H:22]2[CH2:23][CH2:24][C@H:25]([C:28](=[O:30])[NH:45][O:44][CH3:43])[CH2:26][CH2:27]2)[C:17]=1[C:18]([F:21])([F:20])[F:19])=[O:12]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178519894HCID 178519894, compound

Product 1

HCID 178502896HCID 178502896, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of compound 5-3 (75 mg, 0.12 mmol) and O-methylhydroxylamine hydrochloride (10 mg, 0.12 mmol) in DMF (3 mL) were added HATU (55 mg, 0.14 mmol) and DIPEA (0.05 mL, 0.30 mmol) and mixture was stirred at room temperature for 5 h. The reaction mixture was quenched with water and extracted with EtOAc. The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated under reduced pressure to afford crude compound 6-1 (65 mg, 82%) as a white foam. LCMS: 650 (M+H)+.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-549ddcc32232499fa20767ca4098d1d5
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

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