4-Bromobenzyl alcohol → HCID 22013084, compound

HRID 366022Notes

Reaction equation

HRID 366022 reaction equation
[CH2:1]([O:3][CH:4]([O:31][CH2:32][CH3:33])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH2:26][C:27]([OH:29])=[O:28])([NH:15][C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)=[O:17])[C:7]1=[O:30])[CH3:2].Cl.C(N=C=NCCCN(C)C)C.[Br:46][C:47]1[CH:54]=[CH:53][C:50]([CH2:51]O)=[CH:49][CH:48]=1>CS(C)=O.CN(C)C1C=CN=CC=1>[Br:46][C:47]1[CH:54]=[CH:53][C:50]([CH2:51][O:28][C:27]([CH2:26][C:8]2([NH:15][C:16]([NH:18][C:19]3[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=3)=[O:17])[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[N:6]([CH2:5][CH:4]([O:3][CH2:1][CH3:2])[O:31][CH2:32][CH3:33])[C:7]2=[O:30])=[O:29])=[CH:49][CH:48]=1

Participants

6

Reactant 3

HCID 701194-Bromobenzyl alcoholHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 15458211HCID 15458211, compound

Product 1

HCID 22013084HCID 22013084, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

In 10 ml of dimethyl sulfoxide was dissolved 0.336 g of (+)-1-(2,2-diethoxyethyl)-3-hydroxycarbonylmethyl-3-(N'-(4-methylphenyl)ureido)indolin-2-one. To the solution were added successively 0.108 g of 4-dimethylaminopyridine, 0.170 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 0.166 g of 4-bromobenzyl alcohol. The resulting mixture was stirred for 18 hours, followed by concentration. The concentrate was diluted with ethyl ether, washed successively with dilute hydrochloric acid and a saturated aqueous solution of sodium hydrogencarbonate. The organic layer was dried over anhydrous sodium sulfate, and concentrated. The crude product was purified by silica gel column chromatography (hexane/ethyl acetate=2/1) to give 0.219 g (48%) of the title compound as a white powder.

Workup

  1. concentrationfollowed by concentration
  2. additionThe concentrate was diluted with ethyl ether
  3. washwashed successively with dilute hydrochloric acid
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-2e4ab1096fa44a5ca33574e41958f465
Source dataset
uspto-grants-2000_10
Patent number
US06127544

Reaction notes

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