Dimethylamine → HCID 86613907, compound

HRID 1817321Notes

Reaction equation

HRID 1817321 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[CH2:16][CH2:15][C:14]3[C:9](=[C:10]([O:22][CH3:23])[C:11](=[O:21])[N:12]([CH3:20])[C:13]=3[C:17](O)=[O:18])[C:8]2=[O:24])=[CH:4][CH:3]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)[N:45]([CH3:47])[CH3:46])C2C=CC=CC=2N=N1.CNC>CN(C=O)C>[F:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[CH2:16][CH2:15][C:14]3[C:9](=[C:10]([O:22][CH3:23])[C:11](=[O:21])[N:12]([CH3:20])[C:13]=3[C:17]([N:45]([CH3:47])[CH3:46])=[O:18])[C:8]2=[O:24])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 69066186HCID 69066186, compound

Product 1

HCID 86613907HCID 86613907, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-(4-fluorobenzyl)-4-methoxy-2-methyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylic acid (0.14 g, 0.40 mol) in DMF was added BOP (0.515 g, 1.167 mmol) and the dimethylamine (2.0 M in THF) (0.035 g, 0.778 mmol). After 24 hours, the product mixture was concentrated under vacuum. The residual material was purified using reverse phase HPLC eluting with 5-95% acetonitrile (0.1% TFA) in H2O (0.1% TFA) to give 6-(4-fluorobenzyl)-4-methoxy-N,N, 2-trimethyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxamide (ES MS M+1=388). A solution of this product (0.1 g, 0.3 mmol) in CH2Cl2 was treated with HBr (30 wt % in acetic acid) (0.104 g, 1.29 mmol) and after stirring at room temperature for 24 hours, concentrated under vacuum. The residual material was purified using reverse phase HPLC eluting with 5%-95% acetonitrile (0.1% TFA) in H2O (0.1% TFA) to afford the title compound.

Workup

  1. concentrationthe product mixture was concentrated under vacuum
  2. customThe residual material was purified
  3. washeluting with 5-95% acetonitrile (0.1% TFA) in H2O (0.1% TFA)

Sources & evidence

ORD record
ord-0651856336b542ba8ea04b92e2719aef
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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