Benzyl chloroformate → HCID 11709881, compound

HRID 1158619Notes

Reaction equation

HRID 1158619 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[CH3:12][C:13]1[C:18]([NH2:19])=[C:17]([CH3:20])[CH:16]=[C:15]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[N:14]=1.C(N(CC)C(C)C)(C)C>ClCCCl>[CH2:5]([O:4][C:2](=[O:3])[NH:19][C:18]1[C:13]([CH3:12])=[N:14][C:15]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[CH:16][C:17]=1[CH3:20])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 66862754908608-00-4

Product 1

HCID 11709881HCID 11709881, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Benzyl chloroformate (18 mg) was added to a solution of 0.085 M 2,4-dimethyl-6-morpholin-4-yl-pyridin-3-ylamine and 0.17 M N,N-diisopropyl-ethylamine in 1,2-dichloroethane (1 mL). The vial was shaken for 16 hours under argon and concentrated in vacuo. Aqueous sodium hydroxide (1 M, 1 mL) was added and the crude mixture was extracted with isopropyl acetate/tetrahydrofuran (4:1, 2×1 mL). The organic phase was washed with brine (1 mL), concentrated in vacuo and redissolved in 1-propanol/dimethyl sulfoxide (1:1, 0.4 mL) of which 0.2 mL was subjected to preparative LC-MS purification to furnish 4.5 mg (31% yield) of the title compound as an oil. LC-MS (m/z) 342 (MH+); tR=1.58, (UV, ELSD) 99%, 99%.

Workup

  1. concentrationconcentrated in vacuo
  2. additionAqueous sodium hydroxide (1 M, 1 mL) was added
  3. extractionthe crude mixture was extracted with isopropyl acetate/tetrahydrofuran (4:1, 2×1 mL)
  4. washThe organic phase was washed with brine (1 mL)
  5. concentrationconcentrated in vacuo
  6. dissolutionredissolved in 1-propanol/dimethyl sulfoxide (1:1, 0.4 mL) of which 0.2 mL
  7. customwas subjected to preparative LC-MS purification

Sources & evidence

ORD record
ord-4884a055afee4718ae6e8036be1c6e10
Source dataset
uspto-grants-2010_10
Patent number
US07812020B2

Reaction notes

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