Triethylamine → (+/-)-ethyl N-{4-[4,4,4-trifluoro-1-({6-[4-(trifluoromethyl)-1H-pyrazol-1-yl]pyridin-3-yl}amino)butyl]benzoyl}-beta-alaninate

HRID 1520956Notes

Reaction equation

HRID 1520956 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[F:10][C:11]([F:41])([F:40])[CH2:12][CH2:13][CH:14]([C:31]1[CH:39]=[CH:38][C:34]([C:35](O)=[O:36])=[CH:33][CH:32]=1)[NH:15][C:16]1[CH:17]=[N:18][C:19]([N:22]2[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[N:23]2)=[CH:20][CH:21]=1.O.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C>ClCCl.O>[F:41][C:11]([F:10])([F:40])[CH2:12][CH2:13][CH:14]([C:31]1[CH:32]=[CH:33][C:34]([C:35]([NH:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:36])=[CH:38][CH:39]=1)[NH:15][C:16]1[CH:17]=[N:18][C:19]([N:22]2[CH:26]=[C:25]([C:27]([F:28])([F:29])[F:30])[CH:24]=[N:23]2)=[CH:20][CH:21]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86669094HCID 86669094, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 86669095(+/-)-ethyl N-{4-[4,4,4-trifluoro-1-({6-[4-(trifluoromethyl)-1H-pyrazol-1-yl]pyridin-3-yl}amino)butyl]benzoyl}-beta-alaninate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of ethyl 3-aminopropionate hydrochloride (23 mg, 0.19 mmol), (+/−)-4-[4,4,4-trifluoro-1-({6-[4-(trifluoromethyl)-1H-pyrazol-1-yl]pyridin-3-yl}amino)butyl]benzoic acid (44 mg, 0.096 mmol), hydroxybenzotriazole hydrate (15 mg, 0.096 mmol), and triethylamine (55 ul, 0.39 mmol) in dichloromethane (0.96 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (21 mg, 0.11 mmol). The mixture was stirred for 2 hours at ambient temperature. The reaction was diluted with water and the organic layer was separated. The aq. layer was extracted with dichloromethane (2×) and the combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The crude material was used without further purification.

Workup

  1. customthe organic layer was separated
  2. extractionThe aq. layer was extracted with dichloromethane (2×)
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was used without further purification

Sources & evidence

ORD record
ord-d0666ea5f2e9449f848547894f256f74
Source dataset
uspto-grants-2015_07
Patent number
US09073871B2

Reaction notes

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