HCID 89924329, compound → HCID 178484568, compound

HRID 1505713Notes

Reaction equation

HRID 1505713 reaction equation
[CH3:1][N:2]([CH3:34])[C:3]([CH:5]1[CH2:10][CH2:9][CH:8]([N:11]2[CH:15]=[C:14]([C:16]3[CH:17]=[N:18][C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([C:28]5[CH:29]=[N:30][N:31]([CH3:33])[CH:32]=5)[CH:23]=4)=[N:20][CH:21]=3)[CH:13]=[N:12]2)[CH2:7][CH2:6]1)=[O:4]>CN(C=O)C>[CH3:1][N:2]([CH3:34])[C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]2[CH:15]=[C:14]([C:16]3[CH:17]=[N:18][C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([C:28]5[CH:29]=[N:30][N:31]([CH3:33])[CH:32]=5)[CH:23]=4)=[N:20][CH:21]=3)[CH:13]=[N:12]2)[CH2:7][CH2:6]1)=[O:4]

Participants

3

Reactant 1

HCID 89924329HCID 89924329, compound

Product 1

HCID 178484568HCID 178484568, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(4-{2-[3-(1-Methyl-1H-pyrazol-4-yl)-phenyl]-pyrimidin-5-yl}-pyrazol-1-yl)-cyclohexanecarboxylic acid dimethylamide (example 121; 165 mg; 0.33 mmol) was suspended in DMF and filtered to give the title compound as a white solid (50 mg; 20%). 1H NMR (300 MHz, DMSO) δ 9.16 (s, 2H), 8.53 (t, J=1.6 Hz, 1H), 8.49 (s, 1H), 8.26 (s, 1H), 8.24-8.18 (m, 1H), 8.13 (s, 1H), 7.92 (d, J=0.7 Hz, 1H), 7.74-7.67 (m, 1H), 7.51 (t, J=7.8 Hz, 1H), 4.32-4.16 (m, 1H), 3.89 (s, 3H), 3.05 (s, 3H), 2.83 (s, 3H), 2.77-2.63 (m, 1H), 2.20-2.06 (m, 2H), 1.97-1.77 (m, 4H), 1.67-1.48 (m, 2H). HPLC (Chiralpak IC, EtOH:THF 90:10): Rt 6.91 min (purity 98.4%); MS (ESI+): 456.4.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-3e9afb22bf6f47a8839499a55ff52c4e
Source dataset
uspto-grants-2015_12
Patent number
US09216991B2

Reaction notes

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