Diisopropylethylamine → HCID 53640319, compound

HRID 1683114Notes

Reaction equation

HRID 1683114 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:14][CH2:15][OH:16])[CH2:13][CH2:12][NH:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[F:17][C:18]1[CH:19]=[C:20]([CH:24]=[C:25]([F:28])[C:26]=1[F:27])[C:21](O)=[O:22].C(N(CC)C(C)C)(C)C.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:14][CH2:15][OH:16])[CH2:13][CH2:12][N:11]([C:21](=[O:22])[C:20]3[CH:24]=[C:25]([F:28])[C:26]([F:27])=[C:18]([F:17])[CH:19]=3)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 8531543,4,5-Trifluorobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 184644272-(3-(3,4-Dichlorophenyl)pyrrolidin-3-yl)ethanol

Product 1

HCID 53640319HCID 53640319, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Combine 3-(3,4-dichloro-phenyl)-3-(2-hydroxy-ethyl)-pyrrolidine (286 mg, 1.1 mmol), 3,4,5-trifluoro-benzoic acid (1 mmol), N,N-diisopropylethylamine (0.19 mL, 1.1 mmol), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC) (0.21 g, 1.1 mmol), and 1-hydroxybenzotriazole hydrate (HOBT) (0.15 g, 1.1 mmol) in dichloromethane (10 mL). After 18 hour, dilute with dichloromethane and extract with 1M hydrochloric acid solution, 5% sodium bicarbonate solution, and water. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give the title compound: Rf =0.45 (silica gel, 10% methanol/dichloromethane).

Workup

  1. extractionextract with 1M hydrochloric acid solution, 5% sodium bicarbonate solution, and water
  2. dry with materialDry the organic layer over MgSO4
  3. filtrationfilter
  4. customevaporate in vacuo

Sources & evidence

ORD record
ord-cddc832486ca4e889df7c368a4d630e4
Source dataset
uspto-grants-1997_06
Patent number
US05635510

Reaction notes

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