Triethylamine → HCID 22046520, compound

HRID 1830747Notes

Reaction equation

HRID 1830747 reaction equation
[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:8]=1[NH2:14].C(N(CC)CC)C.ClC(Cl)(O[C:27](=[O:33])OC(Cl)(Cl)Cl)Cl.[NH2:35][C:36]1[CH:41]=[N:40][CH:39]=[CH:38][N:37]=1>C1(C)C=CC=CC=1>[CH3:15][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:8]=1[NH:14][C:27]([NH:35][C:36]1[CH:41]=[N:40][CH:39]=[CH:38][N:37]=1)=[O:33]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 78747AminopyrazineHCID 94429TriphosgeneHCID 22046321HCID 22046321, compound

Product 1

HCID 22046520HCID 22046520, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

To a stirred, cooled (about 0° C.) solution of 2-(3-dimethylamino-propoxy)-5-methyl-phenylamine (208 mg, 1.0 mmol) in toluene (3.0 mL) was added triethylamine (140 μL, 1.0 mmol) and triphosgene (98 mg, 0.33 mmol). After stirring for 30 minutes, amino pyrazine (95 mg, 1.0 mmol) was added and the reaction was heated to 65 degrees C. After stirring for 4 hours, the reaction was cooled to room temperature and stirred for 8 hours. The precipitate that formed was filtered, rinsed with toluene (2×1 mL), and dried under reduced pressure (35% yield).

Workup

  1. stirringAfter stirring for 4 hours
  2. temperaturethe reaction was cooled to room temperature
  3. stirringstirred for 8 hours
  4. customThe precipitate that formed
  5. filtrationwas filtered
  6. washrinsed with toluene (2×1 mL)
  7. customdried under reduced pressure (35% yield)

Sources & evidence

ORD record
ord-52afc6be832642318366d37943bf3a0f
Source dataset
uspto-grants-2006_06
Patent number
US07067506B2

Reaction notes

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