1,2-Dichloroethane → HCID 16737313, compound

HRID 254263Notes

Reaction equation

HRID 254263 reaction equation
[C:1]1([CH:7]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:8][CH2:9][N:10]([CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[C:11](=[O:22])[NH:12][C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16](O)=[O:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[CH2:51]([CH2:53][NH2:54])[OH:52]>ClCCl.O>[C:1]1([CH:7]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:8][CH2:9][N:10]([CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[C:11](=[O:22])[NH:12][C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16]([NH:54][CH2:53][CH2:51][OH:52])=[O:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 700EthanolamineHCID 757711-HydroxybenzotriazoleHCID 16737307HCID 16737307, compound

Product 1

HCID 16737313HCID 16737313, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

ylethyl)ureido]benzoic acid (obtained in Example 45) dissolved in dichloromethane are introduced into a 100 mL flask under an argon atmosphere, then HOBt (27 mg, 1.2 eq.), EDC (37 mg, 1.2 eq.), and ethanolamine (12 mg, 1 eq.) are added to the medium. After reacting for 14 hours, the mixture is neutralised with water, then with a saturated NaHCO3 solution and the aqueous phase is extracted with dichloromethane. The organic phases are combined and washed with brine, then, dried over MgSO4 and concentrated. The crude product thus obtained is purified by silica column chromatography (eluent: CH2Cl2/MeOH 99/1 to 96/4). The desired amide, 3-[3-(3,3-diphenylpropyl)-3-(2-morpholin-4-ylethyl)ureido]-N-(2-hydroxyethyl)benzamide, is obtained in a yield of 52%. This procedure is hereinafter called method “J”, route 2.

Workup

  1. additionare introduced into a 100 mL flask under an argon atmosphere
  2. extractionwith a saturated NaHCO3 solution and the aqueous phase is extracted with dichloromethane
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe crude product thus obtained
  7. customis purified by silica column chromatography (eluent: CH2Cl2/MeOH 99/1 to 96/4)

Sources & evidence

ORD record
ord-35ac22747f85483383bb3ed8b5470f2c
Source dataset
uspto-grants-2011_01
Patent number
US07875609B2

Reaction notes

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