Methyl 4-benzamidobenzoate → HCID 178490049, compound

HRID 1092004Notes

Reaction equation

HRID 1092004 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]2[CH:12]=[C:13]([NH2:20])[N:14](C(C)(C)C)[N:15]=2)[CH:6]=[CH:7][CH:8]=1.[C:21]([NH:29][C:30]1[CH:39]=[CH:38][C:33]([C:34](OC)=[O:35])=[CH:32][CH:31]=1)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C[Al](C)C>C1(C)C=CC=CC=1.C(Cl)Cl.C(O)=O>[C:21]([NH:29][C:30]1[CH:31]=[CH:32][C:33]([C:34]([NH:20][C:13]2[NH:14][N:15]=[C:11]([CH2:10][CH2:9][C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)[CH:12]=2)=[O:35])=[CH:38][CH:39]=1)(=[O:28])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 3

HCID 727255Methyl 4-benzamidobenzoateHCID 16682925TrimethylaluminumHCID 574539341-tert-butyl-3-(3-methoxyphenethyl)-1H-pyrazol-5-amine

Product 1

HCID 178490049HCID 178490049, compound

Reagents, catalysts & solvents 3

HCID 284Formic AcidSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
82 °C

Procedure

5-[2-(3-Methoxyphenyl)ethyl]-2-tert-butyl-pyrazol-3-amine (0.2 g, 0.73 mmol) was dissolved in toluene (10 ml) and to this was added methyl 4-benzamidobenzoate (200 mg, 0.80 mmol) and AlMe3 (0.93 ml, 1.8 mmol). The reaction was stirred overnight. The reaction was diluted with DCM (15 ml) and quenched with damp sodium sulfite. The reaction mixture was stirred for 20 mins before being filtered and the solvent removed in vacuo to yield a yellow gum. This gum was dissolved in formic acid (12 ml) and heated at 82° C. overnight. The reaction was evaporated to dryness and the resulting product was passed through a SCX column, eluting initially with methanol followed by 2N ammonia/methanol. After removal of the solvent, a yellow solid was obtained which was triturated with hot acetonitrile to afford a white solid. The solid was filtered and dried (66 mg, 21%); 1H NMR (400.132 MHz, DMSO) δ 2.91 (s, 4H), 3.74 (s, 3H), 6.46 (brs, 1H), 6.77 (d, 1H), 6.83 (s, 2H), 7.20 (t, 1H), 7.64-7.54 (m, 3H), 7.90 (d, 2H), 8.02-7.97 (m, 4H), 10.46 (s, 1H), 10.55 (s, 1H), 12.15 (s, 1H); MS: m/z 441 (MH+).

Workup

  1. customquenched with damp sodium sulfite
  2. stirringThe reaction mixture was stirred for 20 mins
  3. filtrationbefore being filtered
  4. customthe solvent removed in vacuo
  5. customto yield a yellow gum
  6. customThe reaction was evaporated to dryness
  7. washeluting initially with methanol
  8. customAfter removal of the solvent
  9. customa yellow solid was obtained which
  10. customwas triturated with hot acetonitrile
  11. customto afford a white solid
  12. filtrationThe solid was filtered
  13. customdried (66 mg, 21%)

Sources & evidence

ORD record
ord-b772b20cb6214863ae1b81f4d56805c1
Source dataset
uspto-grants-2012_03
Patent number
US08129391B2

Reaction notes

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