4-(Dimethylamino)benzoic acid → HCID 21264389, compound

HRID 567099Notes

Reaction equation

HRID 567099 reaction equation
[CH3:1][N:2]([CH3:12])[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:35][C:36]([F:53])([F:52])[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(C(C)C)CC)(C)C>CN(C)C=O.O>[F:53][C:36]([F:35])([F:52])[C:37]1[CH:38]=[CH:39][C:40]([CH:43]2[C:48]3[CH:49]=[CH:50][S:51][C:47]=3[CH2:46][CH2:45][N:44]2[C:7]([C:6]2[CH:5]=[CH:4][C:3]([N:2]([CH3:1])[CH3:12])=[CH:11][CH:10]=2)=[O:9])=[CH:41][CH:42]=1

Participants

8

Reactant 5

HCID 120924-(Dimethylamino)benzoic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2739390HCID 2739390, compound

Product 1

HCID 21264389HCID 21264389, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-Dimethylaminobenzoic acid (0.20 g, 1.2 mmol) was dissolved in N,N-dimethylformamide (3 ml) and 1-hydroxybenzotriazole (0.20 g, 1.5 mmol) was added. To the resulting mixture N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.28 g, 1.5 mmol) was added and the mixture was stirred at room temperature for 15 minutes. 4-(4-Trifluoromethylphenyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine (0.41 g, 1.5 mmol) followed by diisopropylethylamine (0.42 ml, 2.4 mmol) were added and the mixture was stirred at room temperature for 16 hours. water (2 ml) was added and the mixture was extracted with ethyl acetate (2×5 ml). The combined organic extracts were washed with saturated aqueous sodium chloride solution (4 ml), dried (MgSO4) and concentrated in vacuo to afford the title compound.

Workup

  1. additionwere added
  2. stirringthe mixture was stirred at room temperature for 16 hours
  3. extractionthe mixture was extracted with ethyl acetate (2×5 ml)
  4. washThe combined organic extracts were washed with saturated aqueous sodium chloride solution (4 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f3a89ac4e23d47d09816d2336ba46479
Source dataset
uspto-grants-2001_01
Patent number
US06177443B1

Reaction notes

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