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1-(3-Dimethylaminopropyl)-2-ethylcarbodiimide hydrochloride → (trans)-N"-Cyano-N-(3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-pyrano[3,2-c]pyridin-4-yl)phenylguanidine

HRID 847168
Notes
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Reaction equation

HRID 847168 reaction equation
[C:1]([N:3]=[C:4]([NH:21]C1C=CC=CC=1)[NH:5][C@@H:6]1[C:11]2[CH:12]=C(C#N)[CH:14]=[CH:15][C:10]=2[O:9][C:8]([CH3:19])([CH3:18])[C@H:7]1[OH:20])#[N:2].N[C@@H:29]1[C:34]2C=N[CH:37]=[CH:38][C:33]=2OC(C)(C)[C@H:30]1O.Cl.C[N:44](C)CCCCCN=C=N>CN(C)C=O>[C:1]([N:3]=[C:4]([NH2:21])[N:5]([C:30]1[CH:29]=[CH:34][CH:33]=[CH:38][CH:37]=1)[C@@H:6]1[C:11]2[CH:12]=[N:44][CH:14]=[CH:15][C:10]=2[O:9][C:8]([CH3:18])([CH3:19])[C@H:7]1[OH:20])#[N:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 574828161-(3-Dimethylaminopropyl)-2-ethylcarbodiimide hydrochlorideHCID 67756760(trans)-4-amino-3,4-dihydro-2,2-dimethyl-2H-pyrano[3,2-c]pyridin-3-olHCID 178431174HCID 178431174, compound

Product 1

HCID 88403696(trans)-N"-Cyano-N-(3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-pyrano[3,2-c]pyridin-4-yl)phenylguanidineYield 24.4%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

To a solution of the title A compound from Example 3 (2.2 g, 12.5 mmol) and (trans)-4-amino-3,4-dihydro-2,2-dimethyl-2H-pyrano[3,2-c]pyridin-3-ol (1.1 g, 5.7 mmol) (prepared according to EP 0 205 292 A2) in dimethylformamide (5 ml) under argon, 1-(3-dimethylaminopropyl)-2-ethylcarbodiimide hydrochloride (2.2 g, 10.8 mmol) was added at room temperature. The reaction mixture was stirred at room temperature for 2 hours and then partitioned between water (pH ~11) and ethyl acetate. The organic phase was separated and the aqueous phase was reextracted with ethyl acetate and the combined organic phase was washed with water, aqueous sodium bicarbonate and brine. After drying over anhydrous magnesium sulfate, the solvent was evaporated and the residue was purified by flash chromatography on silica gel (acetone:dichloromethane/1:4) to yield a colorless solid (470 mg) which was crystallized from acetonitrile to provide the title compound, m.p. 233°-236° C.

Workup

  1. custompartitioned between water (pH ~11) and ethyl acetate
  2. customThe organic phase was separated
  3. washthe combined organic phase was washed with water, aqueous sodium bicarbonate and brine
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customthe residue was purified by flash chromatography on silica gel (acetone:dichloromethane/1:4)

Sources & evidence

ORD record
ord-7039612997d045ce9e2a935249c320d4
Source dataset
uspto-grants-1992_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05140031

Reaction notes

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