Pyridine → HCID 59627868, compound

HRID 1256662Notes

Reaction equation

HRID 1256662 reaction equation
[C:1]([O:5][C:6]([N:8]([C:16]1[C:21]([NH2:22])=[CH:20][CH:19]=[C:18]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:17]=1)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1COCC1.N1C=CC=CC=1.Cl[C:41]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:42]>CCOC(C)=O.C(Cl)Cl>[C:1]([O:5][C:6]([N:8]([C:16]1[C:21]([NH:22][C:41]([O:43][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[O:42])=[CH:20][CH:19]=[C:18]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:17]=1)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 1049PyridineHCID 8028TetrahydrofuranHCID 10387Benzyl chloroformateHCID 59627865HCID 59627865, compound

Product 1

HCID 59627868HCID 59627868, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of di-tert-butyl(3-amino-6-phenylpyridin-2-yl)imidodicarbonate (351 mg, 0.910 mmol, theoretical yield from previous reaction), THF (1.82 mL) and methylene chloride (1.82 mL) was cooled 0° C. and pyridine (0.294 mL, 3.64 mmol) and benzyl chloroformate (0.256 mL, 1.82 mmol) were added dropwise. The reaction was stirred for 2 h, diluted with EtOAc and washed with 1M aq. HCl2×, sat. aq. NaHCO3, brine, dried (MgSO4) and concentrated to afford a residue purified via MPLC, silica cartridge, 5-20% EtOAc in heptanes to afford the product as a clear light orange oil. MS cal'd 520 (M+H)+, exp 520 (M+H)+.

Workup

  1. washwashed with 1M aq. HCl2×, sat. aq. NaHCO3, brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customto afford a residue
  5. custompurified via MPLC, silica cartridge, 5-20% EtOAc in heptanes

Sources & evidence

ORD record
ord-285bd0ed3fad42b09a22b51e6db20866
Source dataset
uspto-grants-2013_06
Patent number
US08461189B2

Reaction notes

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