Triethylamine → HCID 68178605, compound

HRID 1520887Notes

Reaction equation

HRID 1520887 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-a0f6aaf283284a9ca7ac6ff27dc1e5d2
Source dataset
uspto-grants-2015_07
Patent number
US09073871B2

Reaction notes

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