Diisopropylethylamine → HCID 66635660, compound

HRID 872099Notes

Reaction equation

HRID 872099 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([F:14])[CH:11]=[C:10]([F:15])[CH:9]=2)[N:5]2[N:16]=[C:17]([CH3:20])[C:18]([I:19])=[C:4]2[N:3]=1.CCN(C(C)C)C(C)C.[NH:30]1[CH2:34][CH2:33][CH2:32][C@H:31]1[CH2:35][OH:36]>C(#N)C>[F:15][C:10]1[CH:9]=[C:8]([C:6]2[N:5]3[N:16]=[C:17]([CH3:20])[C:18]([I:19])=[C:4]3[N:3]=[C:2]([N:30]3[CH2:34][CH2:33][CH2:32][C@H:31]3[CH2:35][OH:36])[CH:7]=2)[CH:13]=[C:12]([F:14])[CH:11]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 640091L-ProlinolHCID 86688006HCID 86688006, compound

Product 1

HCID 66635660HCID 66635660, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Chloro-7-(3,5-difluorophenyl)-3-iodo-2-methylpyrazolo[1,5-a]pyrimidine obtained in Step 3, DIPEA (0.35 mL) and (S)-2-pyrrolidinemethanol (401 mg) are stirred in an acetonitrile (60 mL) solvent for 2.5 hours at 90° C. The reaction solvent is removed by distillation under reduced pressure. The remainder is purified by column chromatography to yield the target compound. 1H NMR (CDCl3, 300 MHz); δ 7.46 (m, 2H), 6.98 (m, 1H), 6.13 (s, 1H), 4.45 (br, 1H), 3.85-3.57 (m, 5H), 2.38 (s, 3H), 2.08-2.04 (m, 3H), 1.77 (m, 1H).

Workup

  1. customThe reaction solvent is removed by distillation under reduced pressure
  2. customThe remainder is purified by column chromatography
  3. customto yield the target compound

Sources & evidence

ORD record
ord-9bf4abbb654c4b71913bdad90b287133
Source dataset
uspto-grants-2015_03
Patent number
US08975264B2

Reaction notes

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