Bis(trimethylsilyl)carbodiimide → HCID 58197808, compound

HRID 473018Notes

Reaction equation

HRID 473018 reaction equation
O=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=3)[C:14]#[N:15])[CH:9]=2)[CH2:4][C:3]21[CH2:26][C:21]1[CH:22]=[N:23][N:24]=[CH:25][C:20]=1[CH2:19]2.C[Si]([N:31]=[C:32]=[N:33][Si](C)(C)C)(C)C>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[C:14]([C:13]1[CH:12]=[C:11]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[CH2:4][C:3]2([CH2:26][C:21]4[CH:22]=[N:23][N:24]=[CH:25][C:20]=4[CH2:19]2)[C:2]3=[N:33][C:32]#[N:31])[CH:18]=[CH:17][CH:16]=1)#[N:15]

Participants

5

Reactant 2

HCID 70473Bis(trimethylsilyl)carbodiimideHCID 58197523HCID 58197523, compound

Product 1

HCID 58197808HCID 58197808, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-(1′-oxo-1′,3′,5,7-tetrahydrospiro[cyclopenta[d]pyridazine-6,2′-inden]-6′-yl)benzonitrile (0.0386 g, 0.11 mmol) in CH2Cl2 (5 mL) was added 0.5 mL of 1.0 M TiCl4 in CH2Cl2 at room temperature. After 1.5 h, 0.4 mL of bis(trimethylsilyl)carbodiimide was added to the yellow solution. The resulting mixture was then stirred at room temperature for 20 h. The mixture was quenched with ice, diluted with CH2Cl2, and dried over Na2SO4. After the solvent was removed under reduced pressure, the crude product was directly used in the next step without further purification. LC-MS tR=1.43 min in 3 min chromatography, m/z 362 (MH+).

Workup

  1. customThe mixture was quenched with ice
  2. additiondiluted with CH2Cl2
  3. dry with materialdried over Na2SO4
  4. customAfter the solvent was removed under reduced pressure
  5. customthe crude product was directly used in the next step without further purification
  6. waitLC-MS tR=1.43 min in 3 min chromatography, m/z 362 (MH+)

Sources & evidence

ORD record
ord-311f2cc183c94eb2a885254b5042bf91
Source dataset
uspto-grants-2014_01
Patent number
US08633212B2

Reaction notes

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