Triethylamine → HCID 69519922, compound

HRID 851962Notes

Reaction equation

HRID 851962 reaction equation
[N:1]1[CH:6]=[C:5]([C:7]([OH:9])=O)[CH:4]=[N:3][CH:2]=1.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(CC)CC.[CH3:44][O:45][C:46]1[CH:51]=[CH:50][C:49]([C@@H:52]([N:54]2[CH2:59][C@@H:58]3[CH2:60][C@H:55]2[CH2:56][NH:57]3)[CH3:53])=[C:48]([CH3:61])[C:47]=1[CH3:62]>CC(N(C)C)=O.CCOC(C)=O>[CH3:44][O:45][C:46]1[CH:51]=[CH:50][C:49]([C@@H:52]([N:54]2[CH2:59][C@@H:58]3[CH2:60][C@H:55]2[CH2:56][N:57]3[C:7]([C:5]2[CH:4]=[N:3][CH:2]=[N:1][CH:6]=2)=[O:9])[CH3:53])=[C:48]([CH3:61])[C:47]=1[CH3:62]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 78346Pyrimidine-5-carboxylic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 69448781HCID 69448781, compound

Product 1

HCID 69519922HCID 69519922, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

Pyrimidine-5-carboxylic acid (14.9 mg, 0.12 mmol), BOP (66.3 mg, 0.15 mmol), and Et3N (34.8 μL, 0.25 mmol) are added to a solution of (1S,4S)-2-[(S)-1-(4-methoxy-2,3-dimethylphenyl)-ethyl]-2,5-diazabicyclo[2.2.1]heptane (26 mg, 0.1 mmol) in anhydrous DMA (1 mL). The reaction mixture is stirred at room temperature for 16 h, diluted with EtOAc, washed with aqueous NaOH 1N (2×8 mL) and brine, dried with Na2SO4, filtered, and concentrated under reduced pressure. The residue is purified by preparative thin layer chromatography eluting with CH2Cl2-MeOH—NH4OH (90-9-1) to afford a yellow oil. LC/MS: 367 (M+1).

Workup

  1. washwashed with aqueous NaOH 1N (2×8 mL) and brine
  2. dry with materialdried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by preparative thin layer chromatography
  6. washeluting with CH2Cl2-MeOH—NH4OH (90-9-1)
  7. customto afford a yellow oil

Sources & evidence

ORD record
ord-c8562c985e8c47508383296bd505010e
Source dataset
uspto-grants-2007_08
Patent number
US07253168B2

Reaction notes

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