Diisopropylethylamine → HCID 53375189, compound

HRID 1500779Notes

Reaction equation

HRID 1500779 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[C:4]([C:9]2[CH:10]=[N:11][N:12]3[CH:17]=[CH:16][N:15]=[CH:14][C:13]=23)[N:3]=1.[F:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:25][NH2:26])=[N:23][CH:24]=1.C(N(C(C)C)CC)(C)C>O1CCCC1>[Cl:8][C:7]1[C:2]([NH:26][CH2:25][C:22]2[CH:21]=[CH:20][C:19]([F:18])=[CH:24][N:23]=2)=[N:3][C:4]([C:9]2[CH:10]=[N:11][N:12]3[CH:17]=[CH:16][N:15]=[CH:14][C:13]=23)=[N:5][CH:6]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 450795431-(5-Fluoropyridin-2-yl)methanamineHCID 86691790HCID 86691790, compound

Product 1

HCID 53375189HCID 53375189, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-(4,5-dichloropyrimidin-2-yl)pyrazolo[1,5-a]pyrazine (Preparation 32, 75 mg, 0.26 mmol), (5-fluoropyridin-2-yl)methanamine (33 mg, 0.26 mmol) and diisopropylethylamine (52 μL, 30 mmol) in tetrahydrofuran (3 mL) was heated to reflux for 72 h. The solvent was then evaporated under reduced pressure and the crude product was purified by reverse phase chromatography (C-18 silica from Waters©, water/acetonitrile/methanol as eluents [0.1% v/v formic acid buffered] 0% to 100%) to give the title compound (37 mg, 39%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 72 h
  3. customThe solvent was then evaporated under reduced pressure
  4. customthe crude product was purified by reverse phase chromatography (C-18 silica from Waters©, water/acetonitrile/methanol as eluents [0.1% v/v formic acid

Sources & evidence

ORD record
ord-3a740ce3c8da4ca4992a2ec84e489236
Source dataset
uspto-grants-2015_12
Patent number
US09206183B2

Reaction notes

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