Diisopropylethylamine → HCID 68026217, compound

HRID 872103Notes

Reaction equation

HRID 872103 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]([CH3:19])[C:17]([I:18])=[C:4]2[N:3]=1.CCN(C(C)C)C(C)C.[NH:29]1[CH2:33][CH2:32][CH2:31][C@H:30]1[CH2:34][OH:35]>C(#N)C>[F:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]2[N:5]3[N:15]=[C:16]([CH3:19])[C:17]([I:18])=[C:4]3[N:3]=[C:2]([N:29]3[CH2:33][CH2:32][CH2:31][C@H:30]3[CH2:34][OH:35])[CH:7]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 640091L-ProlinolHCID 86688008HCID 86688008, compound

Product 1

HCID 68026217HCID 68026217, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Chloro-7-(4-fluorophenyl)-3-iodo-2-methylpyrazolo[1,5-a]pyrimidine (241 mg), DIPEA (0.2 mL) and (S)-2-pyrrolidinemethanol (152 mg) are stirred at 90° C. for 16 hours in an acetonitrile (60 mL) solvent. The reaction solvent is removed by distillation under reduced pressure. The remainder is purified by column chromatography to yield the target compound (172 mg). 1H NMR (CDCl3, 300 MHz); δ 7.92 (m, 2H), 7.22 (m, 2H), 6.10 (s, 1H), 4.45 (br, 1H), 3.85-3.57 (m, 4H), 2.38 (s, 3H), 2.08-2.01 (m, 3H), 1.72 (m, 1H).

Workup

  1. customThe reaction solvent is removed by distillation under reduced pressure
  2. customThe remainder is purified by column chromatography

Sources & evidence

ORD record
ord-bb952bb58b51442184b56838f995f274
Source dataset
uspto-grants-2015_03
Patent number
US08975264B2

Reaction notes

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