Dimethylformamide → HCID 178455798, compound

HRID 271353Notes

Reaction equation

HRID 271353 reaction equation
[C:1]1([CH2:7][CH2:8][CH:9]=[CH:10][C@H:11]2[CH2:16][CH2:15][C@H:14]([NH2:17])[CH2:13][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:19]1[N:24]=[CH:23][N:22]=[C:21]2[NH:25][N:26]=[CH:27][C:20]=12.C(N(C(C)C)CC)(C)C.CN(C)C=O>C(OCC)(=O)C>[C:1]1([CH2:7][CH2:8][CH:9]=[CH:10][C@H:11]2[CH2:12][CH2:13][C@H:14]([NH:17][C:19]3[N:24]=[CH:23][N:22]=[C:21]4[NH:25][N:26]=[CH:27][C:20]=34)[CH2:15][CH2:16]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 2210954-Chloro-1H-pyrazolo[3,4-d]pyrimidineHCID 178511508HCID 178511508, compound

Product 1

HCID 178455798HCID 178455798, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.330 g of trans-4-(4-phenyl-but-1-enyl)-cyclohexyl-amine, 0.222 g of 4-chloro-1H-pyrazolo[3,4-d]pyrimidine (R. K. Robins, J. Amer. Chem. Soc., 78, 784-790 (1956)), 0.376 mL of di-isopropyl-ethylamine and 1.0 mL of dimethyl-formamide were combined and allowed to stir at room temperature for 18 h. The reaction was diluted with ethyl acetate (30 mL) and washed with saturated aqueous sodium bicarbonate. The ethyl acetate extract was dried over sodium sulfate, filtered, concentrated to an oil and chromatographed on silica using ethyl acetate to 5% methanol/ethyl acetate to give a crude product as a foam, (350 mg, 70%). Purification of the crude material (60 mg) using C-18 reversed phase chromatography (1% trifluroacetic acid in acetonitrile/water) gave 0.025 g of pure product as a foam: HRMS=348.2173.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate
  2. extractionThe ethyl acetate extract
  3. dry with materialwas dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to an oil
  6. customchromatographed on silica
  7. customto give a crude product as a foam, (350 mg, 70%)
  8. customPurification of the crude material (60 mg)

Sources & evidence

ORD record
ord-c1cb480c9cb44317a98ba5dc6f14f563
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

Loading…