1,1'-Carbonyldiimidazole → HCID 58941918, compound

HRID 2097642Notes

Reaction equation

HRID 2097642 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:13]2[N:14]=[N:15][S:16][C:17]=2[CH2:18][O:19][Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])=[N:11][OH:12])[CH:5]=[CH:6][C:7]=1[F:8].C1N=CN([C:35](N2C=NC=C2)=[O:36])C=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:35](=[O:36])[O:12][N:11]=[C:10]2[C:13]2[N:14]=[N:15][S:16][C:17]=2[CH2:18][O:19][Si:20]([CH:24]([CH3:26])[CH3:25])([CH:27]([CH3:29])[CH3:28])[CH:21]([CH3:22])[CH3:23])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 178460981HCID 178460981, compound

Product 1

HCID 58941918HCID 58941918, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Into a round bottom flask was added N-(3-chloro-4-fluorophenyl)-N′-hydroxy-5-[(triisopropylsilyl)oxy]methyl-1,2,3-thiadiazole-4-carboximidamide (85.0 mg, 0.185 mmol), anhydrous THF (1.1 mL), and N,N-carbonyldiimidazole (55 mg, 0.34 mmol). The reaction was heated to 70° C. for 2.5 h. The reaction was concentrated in vacuo and the crude purified by flash chromatography to give the desired product (89 mg, 99%). MF═C20H26ClFN4O3SSi; LCMS calculated for C20H27ClFN4O3SSi (M+H)+: m/z=485.2.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe crude purified by flash chromatography

Sources & evidence

ORD record
ord-bbfcb4ba698c407db65dbda40e66c08c
Source dataset
uspto-grants-2013_05
Patent number
US08450351B2

Reaction notes

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