Triethylamine → HCID 178495969, compound

HRID 1004764Notes

Reaction equation

HRID 1004764 reaction equation
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH2:5].[CH2:8]([N:10](CC)CC)C.C([N:17]([CH2:27][CH:28]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH:37]([F:39])[F:38])=[C:32]([O:40][CH:41]2[CH2:45][CH2:44][O:43][CH2:42]2)[CH:31]=1)[CH3:29])[C:18](=[NH:26])OC1C=CC=CC=1)#N>CN(C)C1C=CN=CC=1.O1CCOCC1>[C:8]([N:26]=[C:18]([NH:5][CH2:4][CH:3]([O:6][CH3:7])[O:2][CH3:1])[NH:17][CH2:27][CH:28]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH:37]([F:38])[F:39])=[C:32]([O:40][CH:41]2[CH2:45][CH2:44][O:43][CH2:42]2)[CH:31]=1)[CH3:29])#[N:10]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 89728Aminoacetaldehyde dimethyl acetalHCID 18793516HCID 18793516, compound

Product 1

HCID 178495969HCID 178495969, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 312751,4-DioxaneSolvent2×

Procedure

A mixture of 2,2-dimethoxyethanamine (0.0129 mol), N,N-diethylethanamine (0.023 mol) and N,N-dimethyl-4-pyridinamine (0.0059 mol) in 1,4-dioxane (30 ml) was added to a solution of intermediate 11 (0.0117 mol) in 1,4-dioxane (10 ml), stirred at RT. The reaction mixture was stirred and refluxed overnight. The solvent was evaporated and the residue was washed with water and 1 N NaOH, then extracted with CH2Cl2. The separated organic layer was dried, filtered, and the solvent was evaporated. The residue was purified by open column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 96/4). The pure fractions were collected and the solvent was evaporated, yielding 4.97 g (95%) of (±)-N"-cyano-N-[2-[4-(difluoromethoxy)-3-[(tetrahydro-3-furanyl)oxy]phenyl]propyl]-N'-(2,2-dimethoxyethyl)guanidine (intermediate 12).

Workup

  1. stirringThe reaction mixture was stirred
  2. temperaturerefluxed overnight
  3. customThe solvent was evaporated
  4. washthe residue was washed with water and 1 N NaOH
  5. extractionextracted with CH2Cl2
  6. customThe separated organic layer was dried
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was purified by open column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 96/4)
  10. customThe pure fractions were collected
  11. customthe solvent was evaporated

Sources & evidence

ORD record
ord-9cb1806fdaab4c58b2cef76fd8688de9
Source dataset
uspto-grants-2000_04
Patent number
US06051718

Reaction notes

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