Triethylamine → HCID 178476960, compound

HRID 1525330Notes

Reaction equation

HRID 1525330 reaction equation
[NH2:1][C:2]1[C:3]([OH:14])=[N:4][C:5]([C:8]2[N:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[N:6][CH:7]=1.[CH2:15]([O:17][P:18]([C:23]1[CH:24]=[C:25]([CH2:29][C:30](O)=[O:31])[CH:26]=[CH:27][CH:28]=1)([O:20][CH2:21][CH3:22])=[O:19])[CH3:16].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>CC#N>[OH:14][C:3]1[C:2]([NH:1][C:30](=[O:31])[CH2:29][C:25]2[CH:24]=[C:23]([P:18](=[O:19])([O:17][CH2:15][CH3:16])[O:20][CH2:21][CH3:22])[CH:28]=[CH:27][CH:26]=2)=[CH:7][N:6]=[C:5]([C:8]2[N:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[N:4]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 894625312-(3-(Diethoxyphosphoryl)phenyl)acetic acidHCID 178508022HCID 178508022, compound2×

Product 1

HCID 178476960HCID 178476960, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-amino-2-(pyridazin-3-yl)pyrimidin-4-ol, 35i-h, (0.5 g, 2.6 mmol), 2-(3-(diethoxyphosphoryl)phenyl)acetic acid, 35i-d, (0.7 g, 2.6 mmol), HATU (1.5 g, 3.9 mmol) and Et3N (1.2 g, 11.8 mmol) in MeCN (25 mL) was stirred at room temperature overnight. The reaction mixture was concentrated in vacuum. The residue was extracted with EA (100 mL), and then washed with sat. NH4Cl (50 mL), water (50 mL), and brine (50 mL). The organic layer was concentrated and the residue was purified by column chromatography to afford the product, 35i, (280 mg, 25%). LC-MS (M+H)+ 444.1.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuum
  2. extractionThe residue was extracted with EA (100 mL)
  3. washwashed with sat. NH4Cl (50 mL), water (50 mL), and brine (50 mL)
  4. concentrationThe organic layer was concentrated
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-545dd6bb2e03486290e65689ba1e11c3
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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