Triethylamine → 2-{[3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}-5-methoxybenzamide

HRID 915596Notes

Reaction equation

HRID 915596 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:12]=2[C:13](O)=[O:14])[N:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:28])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+].Cl.C[N:33](C)CCCN=C=NCC.C1C=C2N=NN(O)C2=CC=1.O.C(N(CC)CC)C>CN(C=O)C>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:12]=2[C:13]([NH2:33])=[O:14])[N:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:28])[N:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 100682862-{[3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}-5-methoxybenzoic acid

Product 1

HCID 589586102-{[3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}-5-methoxybenzamideYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-{[3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}-5-methoxybenzoic acid (Example 4) (130 mg, 0.34 mmol) in DMF (5 mL) were added ammonium chloride (22 mg, 0.41 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (79 mg, 0.41 mmol), HOBT hydrate (56 mg, 0.41 mmol), and triethylamine (0.17 mL, 1.20 mmol). The reaction mixture was stirred for 16 h and then concentrated under reduced pressure. The residue was purified by HPLC (45-90% acetonitrile in water) to afford the product (63 mg, 49%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 1.26 (s, 9H), 1.97 (s, 3H), 3.71 (s, 3H), 6.03 (s, 1H), 7.04 (dd, 1H), 7.24-7.37 (m, 6H), 7.44 (s, 1H), 8.05 (s, 1H), 10.01 (s, 1H); ES-MS m/z 379.3 (MH+); HPLC RT (min) 2.83.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by HPLC (45-90% acetonitrile in water)

Sources & evidence

ORD record
ord-e135f25df28747f88da7aa3dbb841b22
Source dataset
uspto-grants-2007_09
Patent number
US07265144B2

Reaction notes

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