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

HRID 1968187Notes

Reaction equation

HRID 1968187 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][NH:14][CH2:15][C:16]2[C:24]3[C:23]([C:25]([OH:27])=O)=[CH:22][CH:21]=[N:20][C:19]=3[NH:18][CH:17]=2)[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=O)C.CN(C1C=CN=CC=1)C>[O:27]=[C:25]1[C:23]2[CH:22]=[CH:21][N:20]=[C:19]3[NH:18][CH:17]=[C:16]([C:24]=23)[CH2:15][N:14]1[CH2:13][CH:10]1[CH2:11][CH2:12][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[CH2:9]1

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 672231593-(((1-(tert-butoxycarbonyl)pyrrolidin-3-yl)methylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid

Product 1

HCID 49841780tert-Butyl 3-((5-oxopyrrolo[4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)methyl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

3-(((1-(tert-Butoxycarbonyl)pyrrolidin-3-yl)methylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid was dissolved in DMF (3 mL). HATU (158 mg, 0.417 mmol) and DMAP (40 mg, 0.278 mmol) were added, and the reaction was stirred at rt for 2 h, concentrated in vacuo, and purified by preparative HPLC eluting with a gradient of 30% to 50% Solvent B in Solvent A to give 14.5 mg of the title compound as a light brown oil. 1H NMR (400 MHz, CD3OD) δ 1.46 (br. s., 9 H) 1.70-1.81 (m, 1 H) 1.99-2.11 (m, 1 H) 2.78 (dt, J=14.34, 7.11 Hz, 1 H) 3.11-3.22 (m, 1 H) 3.32-3.36 (m, 1 H) 3.47-3.57 (m, 2 H) 3.72 (d, J=7.33 Hz, 1 H) 3.76-3.89 (m, 1 H) 5.09 (s, 2 H) 7.38 (s, 1 H) 7.51 (d, J=5.31 Hz, 1H) 8.42 (d, J=5.56 Hz, 1 H). [M+H] found 357.

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified by preparative HPLC
  3. washeluting with a gradient of 30% to 50% Solvent B in Solvent A

Sources & evidence

ORD record
ord-84275552153e49a5bb2ac0b3ed2a9654
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

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