HCID 86695090, compound → HCID 89691360, compound

HRID 1503910Notes

Reaction equation

HRID 1503910 reaction equation
[O:1]=[CH:2][CH2:3][C@H:4]1[CH2:15][CH2:14][C:13]2[S:12][C:11]3[N:10]=[CH:9][N:8]=[C:7]([NH:16][CH:17]4[CH2:22][CH2:21][CH:20]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:19][CH2:18]4)[C:6]=3[C:5]1=2.[CH2:31]([Mg]Br)[CH3:32]>C1COCC1>[OH:1][CH:2]([CH2:31][CH3:32])[CH2:3][C@H:4]1[CH2:15][CH2:14][C:13]2[S:12][C:11]3[N:10]=[CH:9][N:8]=[C:7]([NH:16][CH:17]4[CH2:18][CH2:19][CH:20]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:29])[CH3:28])[CH2:21][CH2:22]4)[C:6]=3[C:5]1=2

Participants

4

Reactant 2

HCID 86695090HCID 86695090, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 89691360HCID 89691360, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a 50-mL round-bottom flask, purged and maintained under an inert atmosphere of nitrogen, was added a solution of 26.3 (244 mg, 0.57 mmol, 1.00 equiv) in distilled THF (10 mL) at 0° C. under nitrogen. Then C2H5MgBr (1 M in THF, 2.85 mL, 5.0 equiv) was added dropwise at 0° C. via syringe. The resulting solution was stirred for an additional 2 h at 0° C., quenched with saturated aqueous NH4Cl and extracted with 3×20 mL of ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was loaded onto a silica gel column with ethyl acetate/petroleum ether (1:5) and purified to give racemic tert-butyl N-(4-[[(3R)-3-(2-hydroxybutyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]amino]cyclohexyl)carbamate (30.1, 130 mg, 50%) as a colorless oil.

Workup

  1. customTo a 50-mL round-bottom flask, purged
  2. temperaturemaintained under an inert atmosphere of nitrogen
  3. customquenched with saturated aqueous NH4Cl
  4. extractionextracted with 3×20 mL of ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. custompurified

Sources & evidence

ORD record
ord-b934a68518ec438793aa799a8fc314ad
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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