Water → HCID 178512452, compound

HRID 623323Notes

Reaction equation

HRID 623323 reaction equation
[CH2:1]1[CH:6]2[CH2:7][C:8]3([NH2:11])[CH2:10][CH:4]([CH2:5]2)[CH2:3][CH:2]1[CH2:9]3.C(OC([NH:19][C:20](=[N:23]C(OC(C)(C)C)=O)SC)=O)(C)(C)C.O>CN(C=O)C.Cl[Hg]Cl>[C:8]12([NH:11][C:20]([NH2:23])=[NH:19])[CH2:10][CH:4]3[CH2:5][CH:6]([CH2:1][CH:2]([CH2:3]3)[CH2:9]1)[CH2:7]2

Participants

6

Reactant 3

HCID 962WaterHCID 2130AmantadineHCID 5466031,3-DI-Boc-2-methylisothiourea

Product 1

HCID 178512452HCID 178512452, compound

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

Amantadine (0.30 g, 2 mmol), HgCl2 (0.54 g, 2 mmol), and 1,3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea (0.58 g, 2 mmol) were stirred in DMF (10 mL) under a N2 atmosphere for 24 h. H2O was added to the reaction mixture, and the white precipitate was removed by filtration. The precipitate was washed with CH2Cl2 twice, and the combined filtrate was extracted with CH2Cl2, washed with brine and dried over MgSO4, concentrated in vacuo, and purified by flash chromatography. The Boc protecting group was removed by 50% TFA/CH2Cl2 for 2 h at RT. Excess TFA was removed by passing N2 through the solution to give a yellow solid which was subsequently purified by flash chromatography (0.41 g, 74% over two steps). 1H-NMR (360 MHz, CD3OD) δ 2.13 (br s, 3H), 1.97 (br s, 6H), 1.76 (br s, 6H); 13C-NMR (90 MHz, CD3OD) δ 160.35, 53.83, 42.45, 36.86, 31.03; ESI-MS: Calculated for C11H19N3 (M+H)+ 194.2. Found: 194.7.

Workup

  1. customthe white precipitate was removed by filtration
  2. washThe precipitate was washed with CH2Cl2 twice
  3. extractionthe combined filtrate was extracted with CH2Cl2
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography
  8. customThe Boc protecting group was removed by 50% TFA/CH2Cl2 for 2 h at RT
  9. customExcess TFA was removed
  10. customto give a yellow solid which
  11. customwas subsequently purified by flash chromatography (0.41 g, 74% over two steps)

Sources & evidence

ORD record
ord-8557071a1acd40979849fb811e0399ee
Source dataset
uspto-grants-2016_04
Patent number
US09301950B2

Reaction notes

Loading…