Triethylamine → HCID 178500697, compound

HRID 2080944Notes

Reaction equation

HRID 2080944 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.[CH:41]1([NH:44][C@H:45]2[CH2:50][CH2:49][C@H:48]([CH2:51][C:52]([O:54][CH3:55])=[O:53])[CH2:47][CH2:46]2)[CH2:43][CH2:42]1>C(Cl)Cl>[CH:41]1([N:44]([C@H:45]2[CH2:50][CH2:49][C@H:48]([CH2:51][C:52]([O:54][CH3:55])=[O:53])[CH2:47][CH2:46]2)[C:4](=[O:6])[C:3]2[CH:7]=[CH:8][C:9]([CH3:11])=[CH:10][C:2]=2[F:1])[CH2:42][CH2:43]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27361452-Fluoro-4-methylbenzoic acidHCID 178500692HCID 178500692, compound

Product 1

HCID 178500697HCID 178500697, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 2-fluoro-4-methylbenzoic acid (0.153 g, 0.994 mmol), 1-hydroxybenzotriazole (0.0639 g, 0.473 mmol), and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.181 g, 0.947 mmol) in CH2Cl2 (5 mL) was added triethylamine (0.396 ml, 2.84 mmol) and methyl 2-(trans-4-(cyclopropylamino)cyclohexyl)acetate (0.200 g, 0.947 mmol). The mixture was stirred at room temperature overnight, diluted with CH2Cl2 (50 mL), and then washed with 10% Na2CO3 and brine. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude product was purified through silica gel chromatography eluting with 18%-25% EtOAc-hexane. The desired amide product was obtained as a colorless oil (0.224 g). MS: 348 (M+1), C20H26FNO3.

Workup

  1. washwashed with 10% Na2CO3 and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified through silica gel chromatography
  5. washeluting with 18%-25% EtOAc-hexane

Sources & evidence

ORD record
ord-b9024163179c4d7aab3dc0b1dade8e78
Source dataset
uspto-grants-2011_04
Patent number
US07932421B2

Reaction notes

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