Dichloromethane → HCID 178478873, compound

HRID 1947265Notes

Reaction equation

HRID 1947265 reaction equation
[CH:1]1([NH:7][C:8]2[C:12]3([CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]3)[N:11]([C:25]3[CH:30]=[CH:29][C:28]([I:31])=[CH:27][CH:26]=3)[C:10](=[O:32])[N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O1CCOCC1.[ClH:39].C(Cl)[Cl:41]>CO>[ClH:41].[ClH:39].[CH:1]1([NH:7][C:8]2[C:12]3([CH2:13][CH2:14][NH:15][CH2:16][CH2:17]3)[N:11]([C:25]3[CH:26]=[CH:27][C:28]([I:31])=[CH:29][CH:30]=3)[C:10](=[O:32])[N:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 204431481,4-Dioxane hydrochlorideHCID 178451556HCID 178451556, compound

Product 1

HCID 178478873HCID 178478873, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of tert-butyl 4-(cyclohexylamino)-1-(4-iodophenyl)-2-oxo-1,3,8-triazaspiro[4.5]dec-3-ene-8-carboxylate (10.9 g, 19.7 mmol) in 4N HCl dioxane (99 mL, 395 mmol) was added small amounts of DCM and MeOH to obtain a solution. After stirring at rt for 1 h, the reaction mixture was concentrated in vacuo, the residue was triturated with diethyl ether and the product was isolated as a white solid by filtration. LRMS (M+1)=453. LC analysis and 1H NMR indicate the presence of an unknown (20%), the titled compound was used as is in subsequent steps, allowing for purification at a later stage.

Workup

  1. customto obtain a solution
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customthe residue was triturated with diethyl ether
  4. customthe product was isolated as a white solid by filtration

Sources & evidence

ORD record
ord-642fa9a573684c36ac4563eb26d540d4
Source dataset
uspto-grants-2013_03
Patent number
US08399473B2

Reaction notes

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