Triethylamine → HCID 69218675, compound

HRID 272690Notes

Reaction equation

HRID 272690 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([Br:10])=[CH:4][C:3]=1[NH:11][C:12]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:13]=1[C:14](O)=[O:15].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>CN(C=O)C>[Br:10][C:5]1[C:6]([O:8][CH3:9])=[CH:7][C:2]2[NH:1][C:14](=[O:15])[C:13]3[CH:17]=[CH:18][C:19]([Cl:21])=[CH:20][C:12]=3[NH:11][C:3]=2[CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59837584HCID 59837584, compound

Product 1

HCID 69218675HCID 69218675, compoundYield 102.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 223F (0.35 g, 0.94 mmol), HATU (0.430 g, 1.13 mmol), and excess Et3N in 4 mL of DMF was stirred overnight. The reaction mixture was partitioned between EtOAc and H2O. The organic layer was washed with brine, dried (MgSO4), filtrated and concentrated to give 0.34 g of the title compound. MS (DCI) m/e 248 (M+H)+; 1H NMR (500 MHz, DMSO-d6) δ 9.89 (s, 1H), 7.90 (s, 1H), 7.67 (d, J=8.42 Hz, 1H), 7.19 (s, 1H), 7.00 (d, J=1.87 Hz, 1H), 6.93 (dd, J=8.42, 2.18 Hz, 1H), 6.75 (s, 1H), 5.22 (s, 2H), 3.73 (s, 3H).

Workup

  1. customThe reaction mixture was partitioned between EtOAc and H2O
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltrated
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f31185db6de946e9b251b6320a6fff98
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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