Benzene → HCID 67124419, compound

HRID 476092Notes

Reaction equation

HRID 476092 reaction equation
O=[C:2]([CH2:8][C:9](=O)[C:10]1[CH:14]=[CH:13][S:12][CH:11]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].C1C=CC=CC=1.[CH3:22][CH:23]([N:25]1[C:29]([NH2:30])=[CH:28][CH:27]=[N:26]1)[CH3:24]>C(O)(=O)C>[CH3:22][CH:23]([N:25]1[C:29]2[N:30]=[C:9]([C:10]3[CH:14]=[CH:13][S:12][CH:11]=3)[CH:8]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:28]=2[CH:27]=[N:26]1)[CH3:24]

Participants

5

Reactant 3

HCID 241BenzeneHCID 10903411-(propan-2-yl)-1H-pyrazol-5-amineHCID 607325531024611-24-2

Product 1

HCID 67124419HCID 67124419, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The title compound was prepared in the same manner as described for intermediate 61 using ethyl 2,4-dioxo-4-(3-thienyl)butanoate (542 mg, 2.397 mmol), benzene (5 mL), 1-(1-methylethyl)-1H-pyrazol-5-amine (300 mg, 2.397 mmol), and acetic acid (5 ml). The crude product was purified using column chromatography (silica gel, eluent: 0 to 100% EtOAc/hexanes) to afford the product as 590 mg (78%). LCMS E-S (M+H)=315.8. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.53 (t, J=6.8 Hz, 3H), 1.66 (d, J=6.8 Hz, 6H), 4.56 (q, J=7.1 Hz, 2H), 5.43 (spt, J=6.7 Hz, 1H), 7.47 (dd, J=5.1, 3.0 Hz, 1H), 7.84-7.95 (m, 1H), 8.08-8.18 (m, 2H), 8.32-8.43 (m, 1H).

Workup

  1. customThe crude product was purified
  2. customto afford the product as 590 mg (78%)

Sources & evidence

ORD record
ord-61a14033c41f4128ad2b3273e29539a6
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Reaction notes

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