Diisopropylethylamine → HCID 86688021, compound

HRID 872130Notes

Reaction equation

HRID 872130 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]([CH:35](C)C)C(C)C.CNC([OH:42])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]([CH2:35][NH:31][CH2:30][CH2:29][OH:42])[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 5247031N-MethylaminoethanolHCID 86688017HCID 86688017, compound

Product 1

HCID 86688021HCID 86688021, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Chloro-2-(ethoxymethyl)-7-(4-fluorophenyl)-3-(4-methylphenyl)pyrazolo[1,5-a]pyrimidine (22 mg), DIPEA (0.1 mL) and N-methylaminoethanol (0.1 mL) are stirred for 12 hours in an acetonitrile (7 mL) solvent at 84° C. The reaction 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 (18 mg).

Workup

  1. customThe reaction 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-579bfa3ec78742a9b714fff377bf660c
Source dataset
uspto-grants-2015_03
Patent number
US08975264B2

Reaction notes

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