Benzene → HCID 68078899, compound

HRID 1522441Notes

Reaction equation

HRID 1522441 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([NH2:7])[N:4]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[N:3]=1.[CH:14]1([C:17](=O)[CH2:18][C:19](=O)[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:16][CH2:15]1.C1C=CC=CC=1>C(O)(=O)C>[CH:14]1([C:17]2[CH:18]=[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:6]3[C:2]([CH3:1])=[N:3][N:4]([C:8]4[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=4)[C:5]=3[N:7]=2)[CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 241BenzeneHCID 47379833-Methyl-1-(pyridin-4-yl)-1H-pyrazol-5-amineHCID 16779961Ethyl 4-cyclopropyl-2,4-dioxobutanoate

Product 1

HCID 68078899HCID 68078899, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The title compound was prepared in the same manner as described for intermediate 30 using 3-methyl-1-(4-pyridinyl)-1H-pyrazol-5-amine (310 mg, 1.780 mmol), ethyl 4-cyclopropyl-2,4-dioxobutanoate (328 mg, 1.780 mmol), benzene (50 mL), and acetic acid (25 mL). The final product was collected as 3.71 (71% overall). LCMS E-S (M+H)=323.5 1H NMR (400 MHz, DMSO-d6) δ ppm 1.15-1.22 (m, 4 H), 1.41 (t, J=7.07 Hz, 3 H), 2.64-2.69 (m, 4 H), 4.47 (q, J=7.07 Hz, 2 H), 7.74 (s, 1 H), 8.27-8.36 (m, 2 H), 8.66-8.71 (m, 2 H).

Workup

  1. customThe final product was collected as 3.71 (71% overall)

Sources & evidence

ORD record
ord-ac58ce0ce1dd44a196d8c0515bbe5813
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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