Benzoic Acid → HCID 21264399, compound

HRID 567096Notes

Reaction equation

HRID 567096 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:10]N1C2C=CC=CC=2N=N1.Cl.[CH3:21][N:22]([CH3:31])[CH2:23][CH2:24]CN=C=NCC.C(N(CC)CC)C.[F:39][C:40]([F:57])([F:56])[C:41]1[CH:46]=[CH:45][C:44]([CH:47]2[C:52]3[CH:53]=[CH:54][S:55][C:51]=3[CH2:50][CH2:49][NH:48]2)=[CH:43][CH:42]=1>CN(C)C=O.C(OCC)(=O)C.O>[CH3:21][N:22]([CH3:31])[CH2:23][CH2:24][O:10][C:5]1[CH:4]=[CH:3][C:2]([C:1]([N:48]2[CH2:49][CH2:50][C:51]3[S:55][CH:54]=[CH:53][C:52]=3[CH:47]2[C:44]2[CH:43]=[CH:42][C:41]([C:40]([F:39])([F:56])[F:57])=[CH:46][CH:45]=2)=[O:9])=[CH:7][CH:6]=1

Participants

9

Reactant 5

HCID 243Benzoic AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2739390HCID 2739390, compound

Product 1

HCID 21264399HCID 21264399, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The above benzoic acid (93 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-Trifluoromethylphenyl)4,5,6,7-tetrahydro-thieno[3,2-c]pyridine (108 mg, 0.38 mmoles) were 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 144 mg (80%) 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-2b2ef9e81e7149f2ab752e2f27bf4f75
Source dataset
uspto-grants-2001_01
Patent number
US06177443B1

Reaction notes

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