Dimethylamine → 2-[11-(3-Chloro-4-fluorobenzyl)-9-hydroxy-1,8,10-trioxo-1,3,4,5,6,8,10,11,12,13-deca-hydro-2H-[1,4]diazocino[2,1-a]-2,6-naphthyridin-2-yl]-N,N-dimethylacetamide

HRID 18019Notes

Reaction equation

HRID 18019 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][C:32]=1[F:33])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([OH:28])[C:10](=[O:27])[N:11]3[CH2:21][CH2:20][CH2:19][CH2:18][N:17]([CH2:22][C:23](O)=[O:24])[C:16](=[O:26])[C:12]3=2)[C:7]1=[O:29].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)[N:52]([CH3:54])[CH3:53])C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.CNC>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][C:32]=1[F:33])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([OH:28])[C:10](=[O:27])[N:11]3[CH2:21][CH2:20][CH2:19][CH2:18][N:17]([CH2:22][C:23]([N:52]([CH3:54])[CH3:53])=[O:24])[C:16](=[O:26])[C:12]3=2)[C:7]1=[O:29]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 59344729HCID 59344729, compound

Product 1

HCID 593447262-[11-(3-Chloro-4-fluorobenzyl)-9-hydroxy-1,8,10-trioxo-1,3,4,5,6,8,10,11,12,13-deca-hydro-2H-[1,4]diazocino[2,1-a]-2,6-naphthyridin-2-yl]-N,N-dimethylacetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of [11-(3-chloro-4-fluorobenzyl)-9-hydroxy-1,8,10-trioxo-1,3,4,5,6,8,10,11,12,13-deca-hydro-2H-[1,4]diazocino[2,1-a]-2,6-naphthyridin-2-yl]acetic acid (25 mg, 0.05 mmol), BOP (28 mg, 0.06 mmol), diisopropylethylamine (7 mg, 0.07 mmol) and dimethylamine (0.11 mL, 2M in THF) in DMF (0.5 mL) was stirred at room temperature overnight. The product mixture was concentrated under vacuum. The residue was subjected to reverse phase column chromatography on C-18 stationary phase eluted with a 95-5% water-acetonitrile gradient. Collection and lyophilization of appropriate fractions afforded the title compound.

Workup

  1. concentrationThe product mixture was concentrated under vacuum
  2. washeluted with a 95-5% water-acetonitrile gradient
  3. customCollection and lyophilization of appropriate fractions

Sources & evidence

ORD record
ord-494e19312afe43139546569ec27687c5
Source dataset
uspto-grants-2010_06
Patent number
US07741315B2

Reaction notes

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