Triethylamine → HCID 86711219, compound

HRID 1475947Notes

Reaction equation

HRID 1475947 reaction equation
CN(C)[CH:3]=[CH:4][CH:5]=[O:6].P(Cl)(Cl)(Cl)=O.[CH2:13]([N:18]([CH2:38][CH2:39][CH:40]([CH3:42])[CH3:41])[C:19]([C:21]1[CH:26]=[CH:25][N:24]2[N:27]=[C:28]([C:30]3[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=3)[CH:29]=[C:23]2[N:22]=1)=[O:20])[CH2:14][CH:15]([CH3:17])[CH3:16].C(N(CC)CC)C>CN(C)C=O.C(Cl)Cl.O>[CH2:38]([N:18]([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[C:19]([C:21]1[CH:26]=[CH:25][N:24]2[N:27]=[C:28]([C:30]3[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=3)[C:29](/[CH:3]=[CH:4]/[CH:5]=[O:6])=[C:23]2[N:22]=1)=[O:20])[CH2:39][CH:40]([CH3:42])[CH3:41]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 791253-(Dimethylamino)-2-propenalHCID 68277118HCID 68277118, compound

Product 1

HCID 86711219HCID 86711219, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(dimethylamino)acrolein (0.22 mL; 218 mg; 2.2 mmol) in N,N-dimethylformamide (3 mL) was added phosphoryl chloride (0.16 mL; 269 mg; 1.76 mmol) and the mixture was stirred at room temperature for 10 min. Then N,N-diisopentyl-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidine-5-carboxamide (180 mg; 0.44 mmol) in N,N-dimethylformamide (2 mL) was added and the mixture was heated to 65° C. for 4 h. Then triethylamine (2 mL) and water (2 mL) were slowly added at 60° C. and the mixture was stirred for 30 min. The mixture was cooled to room temperature and diluted with methylene chloride and water. The aqueous layer was back extracted with methylene chloride and the combined organic layers were washed with water (3×10 mL), brine and concentrated. The residue was purified by flash-chromatography using 5% methanol in methylene chloride as eluant. LCMS m/z 463.3 (M+H)+, ret. time=2.98 min.

Workup

  1. temperaturethe mixture was heated to 65° C. for 4 h
  2. stirringthe mixture was stirred for 30 min
  3. temperatureThe mixture was cooled to room temperature
  4. extractionThe aqueous layer was back extracted with methylene chloride
  5. washthe combined organic layers were washed with water (3×10 mL), brine
  6. concentrationconcentrated
  7. customThe residue was purified by flash-chromatography

Sources & evidence

ORD record
ord-d31e0450d26d419da41991ed446123c7
Source dataset
uspto-grants-2015_04
Patent number
US09018395B2

Reaction notes

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