Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 67086929, compound

HRID 2175046Notes

Reaction equation

HRID 2175046 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]2[CH2:16][CH2:15][C@H:14]3[C@H:11]([NH:12][CH2:13]3)[CH2:10]2)[N:3]=1.[F:17][C:18]1[C:19]([C:27]2[N:32]=[CH:31][CH:30]=[CH:29][N:28]=2)=[C:20]([CH:24]=[CH:25][CH:26]=1)[C:21](O)=[O:22].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH3:8][C:6]1[CH:7]=[C:2]([CH3:1])[N:3]=[C:4]([N:9]2[CH2:16][CH2:15][C@H:14]3[C@H:11]([N:12]([C:21]([C:20]4[CH:24]=[CH:25][CH:26]=[C:18]([F:17])[C:19]=4[C:27]4[N:28]=[CH:29][CH:30]=[CH:31][N:32]=4)=[O:22])[CH2:13]3)[CH2:10]2)[N:5]=1

Participants

5

Reactant 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 670867703-Fluoro-2-(pyrimidin-2-yl)benzoic acid2×HCID 67086933HCID 67086933, compound2×

Product 1

HCID 67086929HCID 67086929, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of (1S,6R)-3-(4,6-dimethylpyrimidin-2-yl)-3,8-diazabicyclo[4.2.0]octane (Intermediate 34, 30 mg, 0.14 mmol), 3-fluoro-2-(pyrimidin-2-yl)benzoic acid (Intermediate 35, 30 mg, 0.14 mmol), and TEA (29 μL, 0.21 mmol) in DMF (1.3 mL) was added HATU (58 mg, 0.15 mmol) After 15 h, the reaction mixture was purified using prep HPLC (agilent, basic) to give 22.4 mg (39%) of the title compound as a clear oil. MS (ESI) mass calcd. For C23H23FN6O, 418.48; m/z found 419.2 [M+H]+. 1H NMR (CDCl3): 8.89-8.57 (m, 2H), 7.50-7.32 (m, 1H), 7.28-7.04 (m, 3H), 6.37-6.23 (m, 1H), 4.76-4.50 (m, 2H), 4.15-3.45 (m, 4H), 3.25-2.73 (m, 2H), 2.43-2.24 (m, 6H), 2.20-1.69 (m, 2H).

Workup

  1. customthe reaction mixture was purified

Sources & evidence

ORD record
ord-b8a74a8ca75f40c0b6549cd4ab669ec3
Source dataset
uspto-grants-2015_06
Patent number
US09062044B2

Reaction notes

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