Trimethylamine → HCID 68766787, compound

HRID 1628463Notes

Reaction equation

HRID 1628463 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[C:3]=1[NH:9][CH2:10][CH2:11][CH2:12][OH:13].[N:14]([C:17]1[C:18]([O:25][CH3:26])=[N:19][C:20]([O:23][CH3:24])=[N:21][CH:22]=1)=[C:15]=S.Cl.CN(C)CCCN=C=NCC.CN(C)C>O1CCCC1.C(OCC)(=O)C.O>[NH2:8][C:4]1[C:3]2[N:9]([CH2:10][CH2:11][CH2:12][OH:13])[C:15]([NH:14][C:17]3[C:18]([O:25][CH3:26])=[N:19][C:20]([O:23][CH3:24])=[N:21][CH:22]=3)=[N:1][C:2]=2[CH:7]=[CH:6][CH:5]=1

Participants

8

Reactant 4

HCID 1146TrimethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68737602HCID 68737602, compoundHCID 86632872HCID 86632872, compound

Product 1

HCID 68766787HCID 68766787, compoundYield 14.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-[(2,6-diaminophenyl)amino]propan-1-ol (Reference Example 115; 363 mg, 2.00 mmol) in tetrahydrofuran (5.0 mL) was added 5-isothiocyanato-2,4-dimethoxypyrimidine (440 mg, 2.20 mmol) portionwise at room temperature. After stirring for 2 hr, N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (422 mg, 2.20 mmol) and trimethylamine (0.331 mL, 2.40 mmol) was added. The mixture was warmed to 50° C. and stirred for additional 3 hr. Water and ethyl acetate were added to the mixture and the insoluble materials were filtered off. The filtrate was extracted with ethyl acetate. Organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with a 0-15% methanol/ethyl acetate gradient mixture. The filtrate was concentrated in vacuo to give the title compound (99 mg, 0.287 mmol, 14%) as a pale yellow amorphous.

Workup

  1. stirringstirred for additional 3 hr
  2. filtrationthe insoluble materials were filtered off
  3. extractionThe filtrate was extracted with ethyl acetate
  4. washOrganic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel eluting with a 0-15% methanol/ethyl acetate gradient mixture
  8. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a1c8efb587d34d01aaccf25b8ca2e7c3
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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