Methanol → HCID 11553747, compound

HRID 349202Notes

Reaction equation

HRID 349202 reaction equation
I[Si](C)(C)C.C(OC([NH:16][C@@H:17]([CH3:46])[CH2:18][NH:19][C:20]1[N:21]([CH2:42][C:43]#[C:44][CH3:45])[C:22]2[C:27](=[O:28])[N:26]([CH2:29][C:30]3[N:39]=[C:38]([CH3:40])[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[N:31]=3)[N:25]=[CH:24][C:23]=2[N:41]=1)=O)C1C=CC=CC=1.[CH3:47]O>ClCCl>[NH2:16][C@@H:17]([CH3:46])[CH2:18][N:19]([C:20]1[N:21]([CH2:42][C:43]#[C:44][CH3:45])[C:22]2[C:27](=[O:28])[N:26]([CH2:29][C:30]3[N:39]=[C:38]([CH3:40])[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[N:31]=3)[N:25]=[CH:24][C:23]=2[N:41]=1)[CH3:47]

Participants

5

Reactant 3

HCID 887MethanolHCID 85247Trimethylsilyl iodide2×HCID 68974497HCID 68974497, compound

Product 1

HCID 11553747HCID 11553747, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

40 μl iodotrimethylsilane are added to a solution of 130 mg (S)-2-[(2-benzyloxycarbonylamino-prop-1-yl)amino]-3-(2-butyn-1-yl)-5-[(4-methyl-quinazolin-2-yl)methyl]-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one in 3 ml dichloromethane. After stirring at ambient temperature for 1 and 3 h, a further 100 μl of iodotrimethylsilane are added on each occasion. The solution is stirred for a further 4 h at ambient temperature and then combined with 5 ml of methanol and evaporated down. Then 1 M hydrochloric acid is added and the aqueous phase is washed twice with dichloromethane. The aqueous phase is made alkaline with sodium carbonate and extracted three times with dichloromethane. The organic extracts are dried over sodium sulphate, the solvent is removed and the residue is purified through silica gel (dichloromethane/methanol 1:0−>3:1).

Workup

  1. stirringThe solution is stirred for a further 4 h at ambient temperature
  2. customevaporated down
  3. additionThen 1 M hydrochloric acid is added
  4. washthe aqueous phase is washed twice with dichloromethane
  5. extractionextracted three times with dichloromethane
  6. dry with materialThe organic extracts are dried over sodium sulphate
  7. customthe solvent is removed
  8. customthe residue is purified through silica gel (dichloromethane/methanol 1:0−>3:1)

Sources & evidence

ORD record
ord-11caafb2af3446e8864dda070d111173
Source dataset
uspto-grants-2007_02
Patent number
US07179809B2

Reaction notes

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