Diisopropylethylamine → HCID 178519577, compound

HRID 1801879Notes

Reaction equation

HRID 1801879 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)=[O:13])[N:3]=1.CCN(C(C)C)C(C)C.[NH:30]1[CH:34]=[CH:33][C:32]([NH2:35])=[N:31]1>CN(C=O)C>[NH:30]1[CH:34]=[CH:33][C:32]([NH:35][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[C:4]([C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=3)=[O:13])[N:3]=2)=[N:31]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 86649047(4-Chloroquinazolin-2-yl)(3-fluorophenyl)methanoneHCID 178418806HCID 178418806, compound

Product 1

HCID 178519577HCID 178519577, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (4-chloroquinazolin-2-yl)(3-fluorophenyl)methanone from Example 1 (57 mg, 0.20 mmol) in DMF (3 mL), DIEA (0.069 mL, 0.4 mmol) and 1H-pyrazol-3-amine (83 mg, 1 mmol) were added. The mixture was stirred at 50° C. for 2 h. The reaction was quenched by adding water and the precipitate was filtered. The crude solid was purified on preparative TLC using DCM/MeOH as mobile phase to afford (4-(1H-pyrazol-3-ylamino)quinazolin-2-yl)(3-fluorophenyl)methanone (18 mg, 27%). 1H NMR (300 MHz, DMSO-d6) δ 6.80 (s, 1H), 7.67-7.61 (m, 4H), 7.92-7.84 (m, 4H), 8.78 (m, 1H), 10.82 (s, 1H), 12.54 (s, 1H); LC-MS (ESI) m/z 334 (M+H)+.

Workup

  1. customThe reaction was quenched
  2. additionby adding water
  3. filtrationthe precipitate was filtered
  4. customThe crude solid was purified on preparative TLC

Sources & evidence

ORD record
ord-953c8336ec4d4fbba436efe642a6f6f4
Source dataset
uspto-grants-2013_01
Patent number
US08349851B2

Reaction notes

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