Benzoic Acid → HCID 21264391, compound

HRID 567098Notes

Reaction equation

HRID 567098 reaction equation
[C:1](O)(=[O:8])[C:2]1[CH:7]=[CH:6]C=[CH:4][CH:3]=1.[OH:10]N1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH2:32]([N:34]([CH2:37][CH3:38])[CH2:35][CH3:36])[CH3:33].[Cl:39][C:40]1[CH:45]=[CH:44][C:43]([CH:46]2[C:51]3[CH:52]=[CH:53][S:54][C:50]=3[CH2:49][CH2:48][NH:47]2)=[CH:42][CH:41]=1.CN(C)[CH:57]=[O:58]>C(OCC)(=O)C.O>[Cl:39][C:40]1[CH:41]=[CH:42][C:43]([CH:46]2[C:51]3[CH:52]=[CH:53][S:54][C:50]=3[CH2:49][CH2:48][N:47]2[C:1]([C:2]2[CH:7]=[CH:6][C:57]([O:58][CH2:33][CH2:32][N:34]3[CH2:37][CH2:38][O:10][CH2:36][CH2:35]3)=[CH:4][CH:3]=2)=[O:8])=[CH:44][CH:45]=1

Participants

9

Reactant 6

HCID 243Benzoic AcidHCID 6228DimethylformamideHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27392694-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

Product 1

HCID 21264391HCID 21264391, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

The above benzoic acid (111 mg, 0.38 mmoles) was suspended in N,N-dimethylformamide (1 mL). 1-Hydroxybenzotriazole (55 mg, 0.42 mmoles), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (79 mg, 0.42 mmoles), and triethylamine (106 μL, 0.76 mmoles) were added and the resulting mixture was shaken at 1000 rpm for 1.5 hour. 4-(4-Chlorophenyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine (100 mg, 0.38 mmoles) was added and the resulting mixture was shaken at 1000 rpm for 3 hours. Water (2 mL) and ethyl acetate (1 mL) were added and the resulting mixture was shaken at 1000 rpm for 15 minutes, The organic phase was evaporated to afford 122 mg (66%) of the title compound as an oil.

Workup

  1. stirringthe resulting mixture was shaken at 1000 rpm for 3 hours
  2. stirringthe resulting mixture was shaken at 1000 rpm for 15 minutes
  3. customThe organic phase was evaporated

Sources & evidence

ORD record
ord-77f0b759333f480e8ab6755fabad7b13
Source dataset
uspto-grants-2001_01
Patent number
US06177443B1

Reaction notes

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