Benzylamine → HCID 21064723, compound

HRID 1243782Notes

Reaction equation

HRID 1243782 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][N:13]=1)[OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.F[B-](F)(F)F.N1(OC(=[N+](C)C)N(C)C)C2C=CC=CC=2N=N1.[CH2:52]([NH2:59])[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1>CCOC(C)=O.CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][CH:10]([C:12]1[CH:20]=[CH:19][C:15]([C:16](=[O:18])[NH:59][CH2:52][C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)=[CH:14][N:13]=1)[OH:11])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 21928101HCID 21928101, compound

Product 1

HCID 21064723HCID 21064723, compoundYield 27.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-(2-tert-Butoxycarbonylamino-1-hydroxy-ethyl)-nicotinic acid (130 mg, 0.461 mmol), diisopropylethylamine (DIPEA) (0.426 mL, 2.44 mmol), [(benzotriazol-1-yloxy)-dimethylamino-methylene]-dimethyl-ammonium tetrafluoroborate (319 mg, 1.00 mmol), and benzyl amine (0.246 mL, 2.30 mmol) were dissolved into 3 mL of dry DMF and stirred overnight. LC-MS indicated formation of the coupled product. The mixture was diluted with 30 mL of EtOAc, the organic phase washed with 2×20 mL H2O and 1×20 mL of brine, dried (MgSO4) filtered and concentrated. The residue was dissolved in CH2Cll2, applied to a SiO2 column and purified (10–30% EtOAc/hexanes) to give 47.8, 27.9% of [2-(5-benzylcarbamoyl-pyridin-2-yl)-2-hydroxy-ethyl]-carbamic acid tert-butyl ester.

Workup

  1. washthe organic phase washed with 2×20 mL H2O and 1×20 mL of brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in CH2Cll2
  6. custompurified (10–30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-f469d294b6c646b4b2ffd97a86c25e38
Source dataset
uspto-grants-2006_10
Patent number
US07119102B2

Reaction notes

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