Diisopropylethylamine → HCID 25226389, compound

HRID 1802467Notes

Reaction equation

HRID 1802467 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]=[C:7]([NH:15][C:16]3[CH:17]=[C:18]([CH:22]=[CH:23][C:24]=3[CH3:25])[C:19]([OH:21])=O)[C:8]3[CH:9]=[CH:10][NH:11][C:12](=[O:14])[C:13]=3[C:4]=2[CH:3]=1.[NH2:28][CH2:29][C@H:30]([OH:32])[CH3:31].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C>CN(C=O)C>[F:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]=[C:7]([NH:15][C:16]3[CH:17]=[C:18]([CH:22]=[CH:23][C:24]=3[CH3:25])[C:19]([NH:28][CH2:29][C@H:30]([OH:32])[CH3:31])=[O:21])[C:8]3[CH:9]=[CH:10][NH:11][C:12](=[O:14])[C:13]=3[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 439938(2R)-1-aminopropan-2-olHCID 25226387HCID 25226387, compound

Product 1

HCID 25226389HCID 25226389, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-[(9-fluoro-1-oxo-1,2-dihydrobenzo[c]-2,6-naphthyridin-5-yl)amino]-4-methylbenzoic acid (Example 1, Step 5) (25 mg, 0.07 mmol) and (2R)-1-aminopropan-2-ol (8 mg, 0.1 mmol) in DMF (0.7 mL) was added BOP (91 mg, 0.21 mmol) and Hunig's base (0.4 mL, 0.21 mmol). The reaction was warmed to 60° C. and the reaction stirred for 18 hours and was then quenched by the addition of sat. aq. NaHCO3 solution. The mixture was extracted with EtOAc and the extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification by silica gel column chromatography (0-10% MeOH/CH2Cl2) afforded the title compound.

Workup

  1. customwas then quenched by the addition of sat. aq. NaHCO3 solution
  2. extractionThe mixture was extracted with EtOAc
  3. washthe extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel column chromatography (0-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-562245aa7cc845f09a7edf208f12e6c7
Source dataset
uspto-grants-2013_01
Patent number
US08349865B2

Reaction notes

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