Diisopropylethylamine → HCID 56933010, compound

HRID 872131Notes

Reaction equation

HRID 872131 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[N:5]2[N:15]=[C:16]([CH2:25][O:26][CH2:27][CH3:28])[C:17]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)=[C:4]2[N:3]=1.[CH3:29][CH2:30][N:31](C(C)C)C(C)C.NC([OH:41])C>C(#N)C>[CH2:27]([O:26][CH2:25][C:16]1[C:17]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)=[C:4]2[N:3]=[C:2]([NH:31][CH2:30][CH2:29][OH:41])[CH:7]=[C:6]([C:8]3[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=3)[N:5]2[N:15]=1)[CH3:28]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 522583Acetaldehyde ammoniaHCID 86688017HCID 86688017, compound

Product 1

HCID 56933010HCID 56933010, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Chloro-2-(ethoxymethyl)-7-(4-fluorophenyl)-3-(4-methylphenyl)pyrazolo[1,5-a]pyrimidine (20 mg), DIPEA (0.1 mL) and aminoethanol (0.1 mL) are stirred for 12 hours in an acetonitrile (7 mL) solvent at 84° C. The solvent is removed by distillation under reduced pressure. The remainder is extracted with ethyl acetate and water. The collected organic layer is washed with brine and dehydrated with anhydrous MgSO4. The solvent is removed by distillation under reduced pressure and the remainder is purified by column chromatography to yield the target compound (15 mg).

Workup

  1. customThe solvent is removed by distillation under reduced pressure
  2. extractionThe remainder is extracted with ethyl acetate and water
  3. washThe collected organic layer is washed with brine
  4. customThe solvent is removed by distillation under reduced pressure
  5. customthe remainder is purified by column chromatography

Sources & evidence

ORD record
ord-3a7d95d1310a435cbc3779dcdfb823f0
Source dataset
uspto-grants-2015_03
Patent number
US08975264B2

Reaction notes

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