Diisopropylethylamine → HCID 66635535, compound

HRID 872115Notes

Reaction equation

HRID 872115 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[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>[Cl:14][C:10]1[CH:9]=[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:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 640091L-ProlinolHCID 86688013HCID 86688013, compound

Product 1

HCID 66635535HCID 66635535, compoundYield 130.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Chloro-7-(3-chlorophenyl)-3-iodo-2-methylpyrazolo[1,5-a]pyrimidine (237 mg), DIPEA (0.2 mL) and (S)-2-pyrrolidinemethanol (120 mg) are stirred at 90° C. for 2 hours in an acetonitrile (15 mL) solvent. The reaction solvent is removed by distillation under reduced pressure. The remainder is purified by column chromatography to yield the target compound (360 mg). 1H NMR (CDCl3, 300 MHz): δ 7.84 (s, 1H), 7.76 (d, J=7.2 Hz, 1H), 7.45 (m, 3H), 6.10 (s, 1H), 4.47 (bs, 1H), 3.83-3.53 (m, 4H), 2.36 (s, 3H) 2.18-1.98 (m, 3H), 1.78 (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-3925186c848b4737b2e38345ac24a10e
Source dataset
uspto-grants-2015_03
Patent number
US08975264B2

Reaction notes

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