Triethylamine → HCID 68178605, compound

HRID 1892728Notes

Reaction equation

HRID 1892728 reaction equation
Cl.C(N=C=NCCCN(C)C)C.[F:13][C:14]([F:41])([F:40])[C:15]1[N:16]=[CH:17][N:18]([C:20]2[CH:39]=[CH:38][C:23]([O:24][CH:25]([C:29]3[CH:37]=[CH:36][C:32]([C:33]([OH:35])=O)=[CH:31][CH:30]=3)[CH2:26][CH2:27][CH3:28])=[CH:22][CH:21]=2)[CH:19]=1.Cl.[NH2:43][CH2:44][CH2:45][C:46]([O:48][CH3:49])=[O:47].ON1C2N=CC=CC=2N=N1.C(N(CC)CC)C>ClCCl>[F:40][C:14]([F:13])([F:41])[C:15]1[N:16]=[CH:17][N:18]([C:20]2[CH:39]=[CH:38][C:23]([O:24][CH:25]([C:29]3[CH:37]=[CH:36][C:32]([C:33]([NH:43][CH2:44][CH2:45][C:46]([O:48][CH3:49])=[O:47])=[O:35])=[CH:31][CH:30]=3)[CH2:26][CH2:27][CH3:28])=[CH:22][CH:21]=2)[CH:19]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 68156746HCID 68156746, compound

Product 1

HCID 68178605HCID 68178605, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (40 mg, 0.21 mmol) was added to a room temperature solution of (+/−)-4-(1-(4-(4-(trifluoromethyl)-1H-imidazol-1-yl)phenoxy)butyl)benzoic acid (80 mg, 0.20 mmol), methyl 3-aminopropanoate hydrochloride (28 mg, 0.20 mmol), 1-hydroxy-7-azabenzotriazole (30 mg, 0.22 mmol), and triethylamine (31 μL, 0.22 mmol) in dichloromethane (2 mL). The solution was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane (20 mL) and washed with water, then brine. The organic layer was dried over magnesium sulfate, filtered and concentrated to give (+/−)-methyl 3-(4-(1-(4-(4-(trifluoromethyl)-1H-imidazol-1-yl)phenoxy)butyl)benzamido)propanoate (89 mg, 90%). 1H NMR (400 MHz, CDCl3, δ): 7.74-7.70 (m, 2H), 7.69-7.66 (s, 1H), 7.44-7.41 (m, 1H), 7.40-7.36 (m, 2H), 7.18-7.13 (m, 2H), 6.91-6.86 (m, 2H), 6.83-6.75 (m, 1H), 5.16-5.12 (m, 1H), 3.72-3.66 (m, 5H), 2.66-2.60 (m, 2H), 2.06-1.93 (m, 1H), 1.86-1.74 (m, 1H), 1.55-1.35 (m, 2H), 0.99-0.91 (m, 3H).

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f0dfe1f844664a3e80286cfa4a463ec6
Source dataset
uspto-grants-2013_08
Patent number
US08507533B2

Reaction notes

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