N-bromobutanimide → HCID 57906440, compound

HRID 420488Notes

Reaction equation

HRID 420488 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([NH2:15])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:24])C(=O)C1>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[C:14]([Br:24])=[CH:13][N:12]=[C:11]([NH2:15])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 57906529(2-aMino-pyridin-4-ylMethyl)-carbaMic acid tert-butyl ester

Product 1

HCID 57906440HCID 57906440, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-18 °C

Procedure

A solution of crude (2-amino-pyridin-4-ylmethyl)-carbamic acid tertbutyl ester (17.55 g) in DMF (50 mL) was cooled to −18° C. (ice/MeOH bath), treated with NBS (12.6 g, 70.7 mmol), and stirred at −18° C. for 1 h. The reaction mixture was diluted in AcOEt (800 mL) and washed with water (2×100 mL) and brine (50 mL). The organic layer was dried over Na2SO4, filtered and evaporated. The residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, hexane/DCM/TBME 100:10:1→TBME 100%) to yield the title compound (13.95 g, 46.2 mmol, 50% for 2 steps) as a pale yellow solid. MS: 303 [M+1]+ HPLC: AtRet=1.10; TLC: RF 0.18 (hexane/DCM/TBME 1:1:2).

Workup

  1. washwashed with water (2×100 mL) and brine (50 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, hexane/DCM/TBME 100:10:1→TBME 100%)

Sources & evidence

ORD record
ord-0e06e95bdb8546c899247350b62cee9a
Source dataset
uspto-grants-2012_01
Patent number
US08097617B2

Reaction notes

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