Triethylamine → HCID 57743088, compound

HRID 1926728Notes

Reaction equation

HRID 1926728 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([CH3:13])[C:10]=2[CH:11]=O)[CH:7]=1.Cl.[NH2:15][CH2:16][CH:17]([CH2:24][CH2:25][CH3:26])[CH2:18][C:19](OCC)=[O:20].C(N(CC)CC)C.[BH4-].[Na+]>CO.O>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([CH3:13])[C:10]=2[CH2:11][N:15]2[CH2:16][CH:17]([CH2:24][CH2:25][CH3:26])[CH2:18][C:19]2=[O:20])[CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 170961496-bromo-2-methylpyrazolo[1,5-a]pyrimidine-3-carbaldehydeHCID 53629151HCID 53629151, compound

Product 1

HCID 57743088HCID 57743088, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 6-bromo-2-methylpyrazolo[1,5-a]pyrimidine-3-carbaldehyde x21 (0.83 mmol, 1 eq, 200 mg) in MeOH (10 ml), is added ethyl 3-(aminomethyl)hexanoate hydrochloride x31 (0.916 mmol, 1.1 eq, 192 mg) and the resulting solution is stirred at room temperature for 5 minutes. Triethylamine (0.916 mmol, 1.1 eq, 128 □l) is then added and the mixture is heated at 65° C. for 1 hour. After this time 1 hour, sodium borohydride is added (0.916 mmol, 1.1 eq, 34 mg). The reaction mixture is then heated at 65° C. for 2 hours. Water (100 ml) is added and the resulting mixture is extracted with CH2Cl2 (3×100 ml). The combined organic layers are combined, washed with brine (100 ml) and dried over MgSO4. Volatiles are removed under reduce pressure and purified by chromatography on silicagel (CH2Cl2/MeOH/NH4OH: 97/3/0.3) to give 130 mg of 1-[(6-bromo-2-methylpyrazolo[1,5-a]pyrimidin-3-yl)methyl]-4-propylpyrrolidin-2-one 184 as a solid.

Workup

  1. temperaturethe mixture is heated at 65° C. for 1 hour
  2. temperatureThe reaction mixture is then heated at 65° C. for 2 hours
  3. extractionthe resulting mixture is extracted with CH2Cl2 (3×100 ml)
  4. washwashed with brine (100 ml)
  5. dry with materialdried over MgSO4
  6. customVolatiles are removed
  7. custompurified by chromatography on silicagel (CH2Cl2/MeOH/NH4OH: 97/3/0.3)

Sources & evidence

ORD record
ord-d66a830d5cdc4aee810878aaf34606b6
Source dataset
uspto-grants-2012_05
Patent number
US08183241B2

Reaction notes

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