Phenylhydrazine → HCID 178504821, compound

HRID 272247Notes

Reaction equation

HRID 272247 reaction equation
[CH2:1]([N:8]([CH2:24][C@H:25]([OH:46])[CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[C:30]([S:42]([CH3:45])(=[O:44])=[O:43])[CH:29]=1)[C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[CH:23]=[CH:22][C:18]([C:19](O)=[O:20])=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[N:48]1[C:52]2[CH:53]=[CH:54][CH:55]=[CH:56][C:51]=2N=[N:49]1.Cl.C(N=C=NCCCN(C)C)C.C1(NN)C=CC=CC=1>ClCCl.C(#N)C.C(N(CC)CC)C>[CH2:1]([N:8]([CH2:24][C@H:25]([OH:46])[CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[C:30]([S:42]([CH3:45])(=[O:44])=[O:43])[CH:29]=1)[C@H:9]1[CH2:10][CH2:11][C@H:12]([C:15]2[CH:16]=[CH:17][C:18]([C:19]([NH:49][NH:48][C:52]3[CH:53]=[CH:54][CH:55]=[CH:56][CH:51]=3)=[O:20])=[CH:22][CH:23]=2)[CH2:13][CH2:14]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 7516PhenylhydrazineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178504822HCID 178504822, compound

Product 1

HCID 178504821HCID 178504821, compoundYield 51.3%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 0.3 g (0.441 mmol) of trans-4-[4-(benzyl{(2S)-3-[4-(benzyloxy)-3-(methylsulfonyl)phenoxy]-2-hydroxypropyl}amino)cyclohexyl]benzoic acid (preparation 4), of 0.78 g (0.91 mmol) of 1-hydroxybenzotriazole, of 0.169 g (0.88 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, of 0.184 ml of triethylamine and of 0.095 g (0.88 mmol) of phenylhydrazine in a mixture of 4 ml of dichloromethane and 0.8 ml of acetonitrile is stirred for 48 hours. The solvents are evaporated under reduced pressure. Dichloromethane and water are added and the organic phase is washed three times with water. The organic phases are dried over magnesium sulfate and concentrated under reduced pressure. The product is obtained in the form of a white solid (0.166 g, 50%) after purification on silica gel (eluent: heptane/ethyl acetate 60/40 for 10 min, 60/40 to 40/60 in 10 min, then 40/60 for 20 min gradient). [M+H+]=734.7

Workup

  1. customThe solvents are evaporated under reduced pressure
  2. additionDichloromethane and water are added
  3. washthe organic phase is washed three times with water
  4. dry with materialThe organic phases are dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1c15759c60054917a4347a7e03ed6a8b
Source dataset
uspto-grants-2008_11
Patent number
US07453010B2

Reaction notes

Loading…