4-Methoxybenzoic Acid → HCID 10252289, compound

HRID 567105Notes

Reaction equation

HRID 567105 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[F:34][C:35]([F:53])([F:52])[O:36][C:37]1[CH:42]=[CH:41][C:40]([CH:43]2[C:48]3[CH:49]=[CH:50][S:51][C:47]=3[CH2:46][CH2:45][NH:44]2)=[CH:39][CH:38]=1.C(N(CC)C(C)C)(C)C>CN(C)C=O.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([N:44]2[CH2:45][CH2:46][C:47]3[S:51][CH:50]=[CH:49][C:48]=3[CH:43]2[C:40]2[CH:39]=[CH:38][C:37]([O:36][C:35]([F:34])([F:53])[F:52])=[CH:42][CH:41]=2)=[O:9])=[CH:10][CH:11]=1

Participants

8

Reactant 5

HCID 74784-Methoxybenzoic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2777349HCID 2777349, compound

Product 1

HCID 10252289HCID 10252289, compoundYield 117%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-Methoxybenzoic acid (0.64 g, 4.2 mmol) was dissolved in N,N-dimethylformamide (25 ml) and 1-hydroxybenzotriazole (0.71 g, 5 mmol) was added followed by N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.96 g, 5 mmol). The resulting mixture was stirred at room temperature for 30 minutes. 4-(4-Trifluoromethoxyphenyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine (1.5 g, 5 mmol) followed by N,N-diisopropylethylamine (1.4 ml, 8.4 mmol) were added and the resulting mixture was stirred at room temperature for 16 hours. Water (10 ml) was added and the mixture was extracted with diethyl ether (3×20 ml). The combined organic extracts were washed with saturated aqueous ammonium chloride (20 ml), dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography over silica gel eluting with a mixture of ethyl acetate and heptane (1:2). The pure fractions were pooled and concentrated in vacuo. The residue was crystallised from a mixture of methyl tert-butyl ether and heptane to afford 2.13 g (98%) of the title compound.

Workup

  1. additionwere added
  2. stirringthe resulting mixture was stirred at room temperature for 16 hours
  3. extractionthe mixture was extracted with diethyl ether (3×20 ml)
  4. washThe combined organic extracts were washed with saturated aqueous ammonium chloride (20 ml)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography over silica gel eluting with a mixture of ethyl acetate and heptane (1:2)
  8. concentrationconcentrated in vacuo
  9. customThe residue was crystallised from a mixture of methyl tert-butyl ether and heptane

Sources & evidence

ORD record
ord-9efe03e4df4c450e9631c7f33b973282
Source dataset
uspto-grants-2001_01
Patent number
US06177443B1

Reaction notes

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