Diisopropylethylamine → HCID 22640301, compound

HRID 2415381Notes

Reaction equation

HRID 2415381 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH:2]1[CH:10]1[C:22]2[NH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]=2[CH2:13][CH2:12][NH:11]1.Cl[C:24]1[N:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)=[CH:26][N:25]=1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH:2]1[CH:10]1[C:22]2[NH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]=2[CH2:13][CH2:12][N:11]1[C:24]1[N:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)=[CH:26][N:25]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 167263772-Chloro-5-(pyridin-2-yl)pyrimidineHCID 22640319HCID 22640319, compound

Product 1

HCID 22640301HCID 22640301, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(2,3-dihydrobenzofuranyl)-2,3,4,9-tetrahydro-1H-β-carboline (prepared according to the process as disclosed in WO97/43287, Intermediate 10, page 25) (1.35 g, 4.66 mmol), 2-chloro-5-(2-pyridinyl)-pyrimidine (893 mg, 4.66 mmol) and N,N-diisopropylethylamine (1.4 mL) were stirred in DMF (10 mL, anhydrous) at 120° C. for 16 h. The resulting mixture was quenched with 10% NaCl and extracted with ethyl acetate. The extracted organic layer was washed with 10% NaCl, brine and then dried with MgSO4. The reaction mixture solvent was evaporated and the residue purified by column chromatography (silica gel, ethyl acetate:hexanes=4:6) to yield the product as a white solid.

Workup

  1. customThe resulting mixture was quenched with 10% NaCl
  2. extractionextracted with ethyl acetate
  3. washThe extracted organic layer was washed with 10% NaCl, brine
  4. dry with materialdried with MgSO4
  5. customThe reaction mixture solvent was evaporated
  6. customthe residue purified by column chromatography (silica gel, ethyl acetate:hexanes=4:6)

Sources & evidence

ORD record
ord-60403ab26f2a4c7ead3d17917171dd1e
Source dataset
uspto-grants-2004_11
Patent number
US06818646B2

Reaction notes

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