4-Hydroxybenzoic Acid → HCID 21264383, compound

HRID 567107Notes

Reaction equation

HRID 567107 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[Cl:33][C:34]1[CH:39]=[CH:38][C:37]([CH:40]2[C:45]3[CH:46]=[CH:47][S:48][C:44]=3[CH2:43][CH2:42][NH:41]2)=[CH:36][CH:35]=1.C(N(CC)C(C)C)(C)C>CN(C)C=O.O>[Cl:33][C:34]1[CH:35]=[CH:36][C:37]([CH:40]2[C:45]3[CH:46]=[CH:47][S:48][C:44]=3[CH2:43][CH2:42][N:41]2[C:6]([C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:10][CH:9]=2)=[O:8])=[CH:38][CH:39]=1

Participants

8

Reactant 5

HCID 1354-Hydroxybenzoic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27392694-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

Product 1

HCID 21264383HCID 21264383, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-Hydroxybenzoic acid (1.3 g, 9.6 mmol) was dissolved in N,N-dimethylformamide (25 ml) and 1-hydroxybenzotriazole (1.3 g, 9.6 mmol) was added followed by N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.8 g, 9.6 mmol), 4-(4-chlorophenyl)4,5,6,7-tetrahydro-thieno[3,2-c]pyridine (2.0 g, 8 mmol) and N,N-diisopropylethylamine (2.5 ml, 16 mmol). The resulting mixture was stirred at room temperature for 16 hours. Water (200 ml) was added and the mixture was extracted with diethyl ether (3×100 ml). The combined organic extracts were washed with saturated aqueous sodium chloride (150 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 (1:1). The pure fractions were pooled and concentrated in vacuo to afford 3.14 9 (100%) of the title compound.

Workup

  1. extractionthe mixture was extracted with diethyl ether (3×100 ml)
  2. washThe combined organic extracts were washed with saturated aqueous sodium chloride (150 ml)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography over silica gel eluting with a mixture of ethyl acetate and heptane (1:1)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7e64be5d74ec4b959497cad2b84ace18
Source dataset
uspto-grants-2001_01
Patent number
US06177443B1

Reaction notes

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