Methyl chloroformate → HCID 67123587, compound

HRID 1887026Notes

Reaction equation

HRID 1887026 reaction equation
Cl.[O:2]=[C:3]1[NH:11][C:10]2[C:5](=[N:6][C:7]([C:12]3[CH:13]=[N:14][N:15]4[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][C:16]=34)=[N:8][CH:9]=2)[N:4]1[C@H:23]1[CH2:28][CH2:27][CH2:26][NH:25][CH2:24]1.Cl[C:30]([O:32][CH3:33])=[O:31].CCN(C(C)C)C(C)C>CN(C=O)C>[C:21]([C:18]1[CH:19]=[CH:20][N:15]2[N:14]=[CH:13][C:12]([C:7]3[N:6]=[C:5]4[C:10]([NH:11][C:3](=[O:2])[N:4]4[C@H:23]4[CH2:28][CH2:27][CH2:26][N:25]([C:30]([O:32][CH3:33])=[O:31])[CH2:24]4)=[CH:9][N:8]=3)=[C:16]2[CH:17]=1)#[N:22]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 67123442HCID 67123442, compound

Product 1

HCID 67123587HCID 67123587, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of example 6 (200 mg, 0.26 mmol) in DMF (2.6 mL), methyl chloroformate (27 mg, 0.28 mmol) and DIPEA (0.068 mL, 0.39 mmol) were added. The reaction mixture was stirred at room temperature overnight. The reaction mixture was evaporated under reduced pressure, dissolved in CH2Cl2, and washed thrice with saturated NaHCO3 aqueous solution. The combined organic phases were dried over MgSO4 and concentrated to dryness. The crude residue was chromatographed on a silica gel flash system (ISCO Combiflash) using CH2Cl2/MeOH mixtures of increasing polarity as eluent to afford 36 mg of the desired product (32% yield).

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. dissolutiondissolved in CH2Cl2
  3. washwashed thrice with saturated NaHCO3 aqueous solution
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. concentrationconcentrated to dryness
  6. customThe crude residue was chromatographed on a silica gel flash system (ISCO Combiflash)
  7. temperatureof increasing polarity as eluent

Sources & evidence

ORD record
ord-82c54cd49efd4685b9b3219f97fcdabc
Source dataset
uspto-grants-2013_08
Patent number
US08501735B2

Reaction notes

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