HCID 67491285, compound → HCID 67491118, compound

HRID 571969Notes

Reaction equation

HRID 571969 reaction equation
C[N:2]([CH3:32])/[CH:3]=[CH:4]/[C:5]([C:7]1[CH:8]=[C:9]([S:17]([NH:20][C@H:21]2[CH2:26][CH2:25][CH2:24][C@@H:23]([N:27]3[CH:31]=[N:30][N:29]=[CH:28]3)[CH2:22]2)(=[O:19])=[O:18])[CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1)=O.N[C:34]1[CH:38]=C[NH:36][N:35]=1>C(O)(=O)C>[N:35]1[N:36]2[C:5]([C:7]3[CH:8]=[C:9]([S:17]([NH:20][C@H:21]4[CH2:26][CH2:25][CH2:24][C@@H:23]([N:27]5[CH:28]=[N:29][N:30]=[CH:31]5)[CH2:22]4)(=[O:18])=[O:19])[CH:10]=[C:11]([C:13]([F:14])([F:16])[F:15])[CH:12]=3)=[CH:4][CH:3]=[N:2][C:32]2=[CH:38][CH:34]=1

Participants

4

Reactant 2

HCID 67491285HCID 67491285, compoundHCID 178418806HCID 178418806, compound

Product 1

HCID 67491118HCID 67491118, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 9b (40.0 mg, 0.085 mmol) and 3-aminopyrazole (8.5 mg, 0.102 mmol) in acetic acid (1.50 mL) was placed in a sealed tube and heated in a microwave reactor at 110° C. for 20 min. After cooling to rt, the reaction mixture was concentrated in vacuo, resuspended in 10% NH4OH/MeOH and reconcentrated. The crude residue was purified by preparative thin layer chromatography on silica gel (10% MeOH/DCM as eluent) to afford the title compound, 9c. m/z (ES) 492 (MH)+; IC50=5.9 nM

Workup

  1. customwas placed in a sealed tube
  2. temperatureAfter cooling to rt
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. customThe crude residue was purified by preparative thin layer chromatography on silica gel (10% MeOH/DCM as eluent)

Sources & evidence

ORD record
ord-b3a4ff8b16314647a4c8cc592c5da1bf
Source dataset
uspto-grants-2015_05
Patent number
US09029377B2

Reaction notes

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