Triethylamine → 2-Chloro-N-(1-hydroxy-cycloheptylmethyl)-5-(2-methyl-thiazol-4-yl)-benzamide

HRID 456894Notes

Reaction equation

HRID 456894 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]([CH3:16])[S:14][CH:15]=2)=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:17][CH2:18][C:19]1([OH:26])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]([CH3:16])[S:14][CH:15]=2)=[CH:7][C:3]=1[C:4]([NH:17][CH2:18][C:19]1([OH:26])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)=[O:6]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 184386481-(Aminomethyl)cycloheptan-1-olHCID 184386562-Chloro-5-(2-methyl-1,3-thiazol-4-yl)benzoic acid

Product 1

HCID 566620342-Chloro-N-(1-hydroxy-cycloheptylmethyl)-5-(2-methyl-thiazol-4-yl)-benzamideYield 33.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-chloro-5-(2-methyl-thiazol-4-yl)-benzoic acid (7 mg, 0.027 mmol), 1-aminomethyl-cycloheptanol (6 mg, 0.03 mmol), 1-hydroxybenzotriazole (5 mg, 0.03 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (6 mg, 0.03 mmol) and triethylamine (5 μL, 0.03 mmol) in N,N-dimethylformamide (0.5 mL) was stirred at room temperature for 16 h. The mixture was diluted with ethyl acetate and washed with 5% citric acid, water, then brine. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography (1:1 ethyl acetate-hexanes) to afford the title compound (3.4 mg).

Workup

  1. washwashed with 5% citric acid, water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (1:1 ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-d0465b06eb6f407d97076930af242ea8
Source dataset
uspto-grants-2007_03
Patent number
US07186742B2

Reaction notes

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