Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 49841776, compound

HRID 1968181Notes

Reaction equation

HRID 1968181 reaction equation
[CH2:1]([C:3]1([N:16]2[CH2:25][C:24]3=[CH:26][NH:27][C:22]4[C:23]3=[C:18]([CH:19]=[CH:20][N:21]=4)[C:17]2=[O:28])[CH2:8][CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5][CH2:4]1)[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C1C=CN=CC=1.CN(C=O)C>[CH2:1]([C:3]1([N:16]2[CH2:25][C:24]3=[CH:26][NH:27][C:22]4[C:23]3=[C:18]([CH:19]=[CH:20][N:21]=4)[C:17]2=[O:28])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)[CH3:2]

Participants

5

Reactant 2

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 49841775tert-butyl 4-ethyl-4-(5-oxopyrrolo[4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)piperidine-1-carboxylate

Product 1

HCID 49841776HCID 49841776, compoundYield 79.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

tert-Butyl 4-ethyl-4-(5-oxopyrrolo[4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)piperidine-1-carboxylate (50 mg, 0.124 mmol), HATU (94 mg, 0.248 mmol), and 4-dimethylaminopyridine (46 mg, 0.373 mmol) were stirred in DMF (3 mL) at room temperature for 1 h. The solution was concentrated in vacuo and dissolved in DCM (3 mL) and TFA (1 mL) and allowed to stir at room temperature for 1 h. The solution was concentrated in vacuo and was purified via preparative HPLC 10% to 30% B in A and gave 28 mg of the title compound as its TFA salt. 1H NMR (400 MHz, CD3OD) δ 7.36 (m, 1H), 7.27 (m, 1H), 5.04 (s, 2H), 3.22-3.34 (m, 2H), 3.19-3.21 (m, 2H), 2.95-2.98 (m, 2H), 2.13-2.23 (m, 4H), 0.97 (t, 3H, J=7.6 Hz). [M+H] found 285.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutiondissolved in DCM (3 mL)
  3. concentrationThe solution was concentrated in vacuo
  4. customwas purified via preparative HPLC 10% to 30% B in A

Sources & evidence

ORD record
ord-d5d737fa75644f079da50dd85804170a
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

Loading…