Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 10240028, compound

HRID 2307934Notes

Reaction equation

HRID 2307934 reaction equation
[CH3:1][C:2]1([CH3:23])[C:11]2[C:6](=[CH:7][C:8]([CH3:22])=[C:9]([CH2:13][C:14]3[O:18][C:17]([C:19]([OH:21])=O)=[CH:16][CH:15]=3)[C:10]=2[CH3:12])[O:5][CH2:4][CH2:3]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:48][O:49][C:50]1[C:55]([NH2:56])=[C:54]([O:57][CH3:58])[N:53]=[C:52]([NH:59][CH2:60][CH2:61][CH2:62][N:63]2[CH2:68][CH2:67][O:66][CH2:65][CH2:64]2)[N:51]=1>CN(C=O)C>[CH3:58][O:57][C:54]1[C:55]([NH:56][C:19]([C:17]2[O:18][C:14]([CH2:13][C:9]3[C:10]([CH3:12])=[C:11]4[C:6](=[CH:7][C:8]=3[CH3:22])[O:5][CH2:4][CH2:3][C:2]4([CH3:1])[CH3:23])=[CH:15][CH:16]=2)=[O:21])=[C:50]([O:49][CH3:48])[N:51]=[C:52]([NH:59][CH2:60][CH2:61][CH2:62][N:63]2[CH2:68][CH2:67][O:66][CH2:65][CH2:64]2)[N:53]=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 11666527HCID 11666527, compoundHCID 22602997HCID 22602997, compound

Product 1

HCID 10240028HCID 10240028, compoundYield 7.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 50-mL round-bottom flask, 5-[(4,4,5,7-tetramethyl-3,4-dihydro-2H-chromen-6-yl)methyl]-2-furoic acid (114.53 mg, 0.364 mmol) and HATU (152.36 mg, 0.400 mmol) were dissolved in DMF (2 mL). To this solution 4,6-dimethoxy-N2-(3-morpholin-4-ylpropyl)pyrimidine-2,5-diamine (209) (108.32 364 mmol) and triethylamine,(91.98 mg, 0.911 mmol) were added. The reaction mixture was stirred at room temperature overnight. The solution was filtered through a PTFE (polytetrafluoroethylene) membrane micro filter. The crude mixture was purified by HPLC C18 column, eluted with aceonitrile/water/0.1% ACOH (30% ACN-70% CAN over 30 min) to yield N-{4,6-dimethoxy-2-[(3-morpholin-4-ylpropyl)amino]pyrimidin-5-yl}-5-[(4,4,5,7-tetramethyl-3,4-dihydro-2H-chromen-6-yl)methyl]-2-furamide (I1) (15.9 mg, 7% yield). 1H NMR (CDCl3) δ 1.31(s, 6H), 1.80(m, 4H, J=6.80, 6.42, 6.04 Hz), 2.15(s, 3H), 2.23(s, 3H), 2.49(m, 6H), 2.63(t, 2H, J=6.80 Hz), 3.49(q, 2H, J=6.04, 5.67 Hz), 3.75(t, 4H, J=4.53 Hz), 3.87(s, 6H), 3.98(s, 2H), 5.74(s, 1H), 5.80(d, 1H, J=3.02 Hz), 6.56(s, 1H), 7.01 (d, 1H, J=3.02 Hz), 7.05(s, 1H). (M+1) 594.2.

Workup

  1. filtrationThe solution was filtered through a PTFE (polytetrafluoroethylene) membrane micro filter
  2. customThe crude mixture was purified by HPLC C18 column
  3. washeluted with aceonitrile/water/0.1% ACOH (30% ACN-70% CAN over 30 min)

Sources & evidence

ORD record
ord-2c8b5a1fe08a4499a889be179314ae50
Source dataset
uspto-grants-2004_12
Patent number
US06833372B2

Reaction notes

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