Triethylamine → HCID 67256058, compound

HRID 1821755Notes

Reaction equation

HRID 1821755 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([O:11][CH2:12][CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])[CH:5]=1.C(N(CC)CC)C.ClC(Cl)(O[C:30](=[O:36])OC(Cl)(Cl)Cl)Cl.[CH3:38][C:39]1[N:40]=[CH:41][C:42]([NH2:45])=[N:43][CH:44]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:30]([NH:45][C:42]2[CH:41]=[N:40][C:39]([CH3:38])=[CH:44][N:43]=2)=[O:36])=[C:6]([O:11][CH2:12][CH2:13][CH2:14][N:15]([CH3:16])[CH3:17])[CH:5]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 3132155-Methylpyrazin-2-amineHCID 67254489HCID 67254489, compound

Product 1

HCID 67256058HCID 67256058, compoundYield 40%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

To a stirred, cooled (about 0° C.) solution of 4-amino-3-(3-dimethylamino-propoxy)-benzoic acid methyl ester (252 mg, 1.0 mmol) in toluene (3.0 mL) was added triethylamine (139 μL, 1.0 mmol) and triphosgene (98 mg, 0.33 mmol). After stirring for 30 minutes, 5-methyl-2-amino pyrazine (109 mg, 1.0 mmol) was added and the reaction was heated to 65 degrees C. The reaction was allowed to cool to room temperature, then diluted with ethyl acetate (50 mL) and water (50 mL). A precipitate formed which was filtered and dried under reduced pressure to yield the desired material as a white solid (40% yield). 1H-NMR (400 MHz, d6-DMSO) δ 8.62 (br s, 1H), 8.41 (d, 1H), 8.19 (s, 1H), 7.59 (d, 1H), 7.49 (s, 1H), 4.15 (t, 2H), 3.81 (s, 3H), 2.42 (m, 5H), 2.18 (s, 6H), 2.01 (m, 2H).

Workup

  1. temperatureto cool to room temperature
  2. customA precipitate formed which
  3. filtrationwas filtered
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-4c79d2d72ca6495683c7c3e939d1ccec
Source dataset
uspto-grants-2009_10
Patent number
US07608618B2

Reaction notes

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