Diethyl Ether → HCID 71765373, compound

HRID 1400002Notes

Reaction equation

HRID 1400002 reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:14][C:13]([N:22]3[CH:26]=[C:25]([CH:27]=[O:28])[N:24]=[N:23]3)=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2].Br[Mg][CH3:31].CCOCC.[NH4+].[Cl-]>C1COCC1>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:14][C:13]([N:22]3[CH:26]=[C:25]([CH:27]([OH:28])[CH3:31])[N:24]=[N:23]3)=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 86696911HCID 86696911, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 71765373HCID 71765373, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a suspension of iv (40 mg, 0.1 mmol) in THF (0.7 mL) was added bromo(methyl)magnesium 3M in Et2O (0.250 mL, 0.1 mmol) and the mixture heated at 40° C. for 1 h. NH4Cl (sat. aq.) was added and the mixture extracted with DCM:IPA (5:1). The organic layers were washed with brine and then concentrated in vacuo to give a crude product that was purified by reverse phase SP4 (ACN gradient in H2O) affording Compound 9 (1.9 mg, 4%).

Workup

  1. extractionthe mixture extracted with DCM:IPA (5:1)
  2. washThe organic layers were washed with brine
  3. concentrationconcentrated in vacuo
  4. customto give a crude product that
  5. customwas purified by reverse phase SP4 (ACN gradient in H2O)

Sources & evidence

ORD record
ord-a0db0eff9d9b4f9592a45c8eda05907e
Source dataset
uspto-grants-2014_12
Patent number
US08906902B2

Reaction notes

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