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

HRID 1968180Notes

Reaction equation

HRID 1968180 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([NH:16][CH2:17][C:18]2[C:26]3[C:25]([C:27]([OH:29])=O)=[CH:24][CH:23]=[N:22][C:21]=3[NH:20][CH:19]=2)([CH2:14][CH3:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[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>[CH2:14]([C:11]1([N:16]2[CH2:17][C:18]3=[CH:19][NH:20][C:21]4[C:26]3=[C:25]([CH:24]=[CH:23][N:22]=4)[C:27]2=[O:29])[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]1)[CH3:15]

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 672237873-((1-(tert-butoxycarbonyl)-4-ethylpiperidin-4-ylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid

Product 1

HCID 49841775tert-butyl 4-ethyl-4-(5-oxopyrrolo[4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

3-((1-(tert-Butoxycarbonyl)-4-ethylpiperidin-4-ylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid (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 to give the title compound which was used without further purification.

Workup

  1. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-a592ff3a48234924ace155c34059ffbc
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

Loading…