Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → Methyl N-(Benzo[b][1,8]napthyridin-2(1H)-one 3-yl)-N-(2-boc-aminoethyl)glycinate

HRID 1167383Notes

Reaction equation

HRID 1167383 reaction equation
[C:1]([CH:8]([NH2:16])[CH2:9][NH:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH:17]1[C:26]2[N:25]=[C:24]3[CH:27]=[CH:28][CH:29]=[CH:30][C:23]3=[CH:22][C:21]=2[CH:20]=[CH:19][C:18]1=[O:31].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[NH:17]1[C:26]2[N:25]=[C:24]3[CH:27]=[CH:28][CH:29]=[CH:30][C:23]3=[CH:22][C:21]=2[CH:20]=[C:19]([N:10]([CH2:9][CH:8]([NH2:16])[C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:11][C:12]([O:14][CH3:15])=[O:13])[C:18]1=[O:31]

Participants

5

Reactant 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 5355541Benzo[b][1,8]naphthyridin-2(1H)-oneHCID 53740519Methyl N-(2-Boc-aminoethyl)glycinate

Product 1

HCID 86759167Methyl N-(Benzo[b][1,8]napthyridin-2(1H)-one 3-yl)-N-(2-boc-aminoethyl)glycinateYield 23.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl N-(2-Boc-aminoethyl)glycinate (0.812 g, 3.5 mmol) was dissolved in DMF (10 mL) and benzo[b][1,8]napthyridin-2(1H)-one 3 acetic acid (883 mg, 3.5 mmol) was added. The mixture was cooled in an ice bath and HBTU (1.52 g, 4.0 mmol) was added. After 1 hour the ice bath was removed and the mixture was stirred overnight at room temperature. The mixture was evaporated in vacuo, redissolved in dichloromethane (100 mL) and washed with saturated aqueous NaHCO3 (2×50 mL). The organic phase was dried (MgSO4) and evaporated in vacuo. The crude product was purified on a silica column eluted with dichloromethane/methanol (97:3, v/v). Fractions containing the product were pooled and evaporated in vacuo to give 345 mg (21%) of the title compound as a tan solid.

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. customAfter 1 hour the ice bath was removed
  3. customThe mixture was evaporated in vacuo
  4. dissolutionredissolved in dichloromethane (100 mL)
  5. washwashed with saturated aqueous NaHCO3 (2×50 mL)
  6. dry with materialThe organic phase was dried (MgSO4)
  7. customevaporated in vacuo
  8. customThe crude product was purified on a silica column
  9. washeluted with dichloromethane/methanol (97:3
  10. additionFractions containing the product
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-a138e4d4609d4a13807f0ad06ef5247d
Source dataset
uspto-grants-2003_09
Patent number
US06617422B1

Reaction notes

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