Diisopropylethylamine → HCID 178522412, compound

HRID 1466644Notes

Reaction equation

HRID 1466644 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][CH:15]2[CH2:17][CH2:16]2)=[C:6]([C:8]2[C:12]([NH2:13])=[CH:11][NH:10][N:9]=2)[CH:7]=1.[N:18]1[N:22]2[CH:23]=[CH:24][CH:25]=[N:26][C:21]2=[C:20]([C:27](Cl)=[O:28])[CH:19]=1.CCN(C(C)C)C(C)C>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][CH:15]2[CH2:17][CH2:16]2)=[C:6]([C:8]2[C:12]([NH:13][C:27]([C:20]3[CH:19]=[N:18][N:22]4[CH:23]=[CH:24][CH:25]=[N:26][C:21]=34)=[O:28])=[CH:11][NH:10][N:9]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 19623233Pyrazolo[1,5-a]pyrimidine-3-carbonyl chlorideHCID 178508049HCID 178508049, compound

Product 1

HCID 178522412HCID 178522412, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(5-chloro-2-cyclopropoxyphenyl)-1H-pyrazol-4-amine (0.2 g, 0.8 mmol) was dissolved in 15 mL of anhydrous THF. Pyrazolo[1,5-a]pyrimidine-3-carbonyl chloride (0.17 g, 0.96 mmol) was added followed by DIPEA (0.2 g, 1.6 mmol). The mixture was stirred at room temperature for 2 h, then evaporated to dryness. The residue was purified by silica gel chromatography (EtOAc as eluant) to afford 0.3 g of the title compound. Yield: 95%. 1H NMR (DMSO-d6, 400 MHz) δ: 12.93 (d, 1H), 9.56 (d, J=5.2 Hz, 1H), 9.34 (d, J=7.2 Hz, 1H), 8.75-8.74 (m, 1H), 8.65 (s, 1H), 8.22 (s, 0.5H), 8.05 (s, 0.5H), 7.55-7.25 (m, 4H), 3.97-3.94 (m, 1H), 0.70-0.44 (m, 4H).

Workup

  1. customevaporated to dryness
  2. customThe residue was purified by silica gel chromatography (EtOAc as eluant)

Sources & evidence

ORD record
ord-03da5a3262cd45168dd20c9bd2142ae9
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

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