Bis(trimethylsilyl)carbodiimide → HCID 58197808, compound

HRID 1503443Notes

Reaction equation

HRID 1503443 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-b9058fe7064f4f7da76c095d1dfe541a
Source dataset
uspto-grants-2015_12
Patent number
US09212153B2

Reaction notes

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