Methylamine → HCID 58318616, compound

HRID 473445Notes

Reaction equation

HRID 473445 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:11]1[C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:19]([C:27]([OH:29])=O)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][N:17]=2)[N:12]=1)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C[N:33]([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)[CH2:32]C1.F[P-](F)(F)(F)(F)F.CN.C(N(C(C)C)C(C)C)C>CN(C=O)C>[CH3:32][NH:33][C:27]([C:19]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][N:17]=2)[N:12]=[C:11]([CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:4])[CH3:3])[CH3:10])[C:20]=1[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:29]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 58318627HCID 58318627, compound

Product 1

HCID 58318616HCID 58318616, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(1-(tert-butoxycarbonylamino)ethyl)-3-phenyl-1,5-naphthyridine-4-carboxylic acid (205 mg, 0.52 mmol) in DMF (5 mL) was added PyBop (407 mg, 1.5 mmol), methanamine (0.52 mL, 2.0 eq) and N-ethyl-N-isopropyl-propan-2-amine (0.18 mL, 2.0 eq). The resulting mixture was stirred at room temperature overnight. The mixture was partitioned between water (10 mL) and EtOAc (15 mL). The water layer was extracted with EtOAc (5 mL×2). The combined organics were washed with water (10 mL×2), 0.5 N NaOH (5 mL×2), water (5 mL×2), brine (5 mL) and dried over sodium sulfate. Removal of solvents followed with column chromatography on silica gel (EtOAc/hexane, up to 2/1) to give a white solid. Mass Spectrum (ESI) m/e=407 (M+1).

Workup

  1. customThe mixture was partitioned between water (10 mL) and EtOAc (15 mL)
  2. extractionThe water layer was extracted with EtOAc (5 mL×2)
  3. washThe combined organics were washed with water (10 mL×2), 0.5 N NaOH (5 mL×2), water (5 mL×2), brine (5 mL)
  4. dry with materialdried over sodium sulfate
  5. customRemoval of solvents
  6. customto give a white solid

Sources & evidence

ORD record
ord-b0020b33bd794c7bbfe2eaa4635813db
Source dataset
uspto-grants-2014_01
Patent number
US08633313B2

Reaction notes

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