Diisopropylethylamine → HCID 178460986, compound

HRID 415990Notes

Reaction equation

HRID 415990 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:33]2[CH:38]=[CH:37][C:36]([C:39](O)=[O:40])=[CH:35][CH:34]=2)[CH:5]=[C:6]([Cl:32])[C:7]=1[CH2:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C@H:14]2[CH2:19][CH2:18][C@@H:17]([O:20][Si:21]([CH:28]([CH3:30])[CH3:29])([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23])[CH2:16][CH2:15]2)[C:10]1=[O:31].[F:42][CH2:43][CH2:44][N:45]1[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]1.C(N(C(C)C)CC)(C)C.Cl.CN(C)CCCN=C=NCC>ClCCl.C(=O)(O)[O-].[Na+]>[Cl:32][C:6]1[CH:5]=[C:4]([C:33]2[CH:38]=[CH:37][C:36]([C:39]([N:48]3[CH2:49][CH2:50][N:45]([CH2:44][CH2:43][F:42])[CH2:46][CH2:47]3)=[O:40])=[CH:35][CH:34]=2)[CH:3]=[C:2]([Cl:1])[C:7]=1[CH2:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C@H:14]2[CH2:19][CH2:18][C@@H:17]([O:20][Si:21]([CH:22]([CH3:24])[CH3:23])([CH:28]([CH3:29])[CH3:30])[CH:25]([CH3:26])[CH3:27])[CH2:16][CH2:15]2)[C:10]1=[O:31]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 210826721-(2-Fluoroethyl)piperazineHCID 178460987HCID 178460987, compound

Product 1

HCID 178460986HCID 178460986, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Treat a mixture of 3′,5′-dichloro-4′-[(R)-2-oxo-cis-1-(4-triisopropylsilanyloxy-cyclohexyl)-pyrrolidin-3-ylmethyl]-biphenyl-4-carboxylic acid (4 g, 5.46 mmol), 1-(2-fluoro-ethyl)-piperazine (2.97 g, 12.12 mmol) and diisopropylethylamine (3.13 g, 24.24 mmol) in 125 mL dichloromethane with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (3.1 g, 16.16 mmol) and stir at room temperature overnight. Dilute with 150 mL saturated sodium bicarbonate and separate layers. Wash the organic layer with 150 mL water then 100 mL brine. Extract the combined aqueous layers with 100 mL dichloromethane and combine with original organic layer. Dry over sodium sulfate, filter, concentrate, and purify via silica chromatography to give 4 g (67%) product as a foam: MS (m/z): 732 (M+).

Workup

  1. additionTreat
  2. customseparate layers
  3. washWash the organic layer with 150 mL water
  4. extractionExtract the combined aqueous layers with 100 mL dichloromethane
  5. dry with materialDry over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate
  8. custompurify via silica chromatography

Sources & evidence

ORD record
ord-325bf448a4794b97910d23da587a396d
Source dataset
uspto-grants-2012_01
Patent number
US08088776B2

Reaction notes

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