Dimethylformamide → (+/-)-N-[3-[2-[2-(dibenzofuran-3-yloxy)ethylamino]-1-hydroxyethyl]phenyl]methanesulfonamide Hydrochloride

HRID 635414ノート

反応式

HRID 635414 の反応式
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[C:3]([O:14][CH2:15][CH2:16][NH2:17])[CH:2]=1.Br[CH2:19][C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH:23]=1)=[O:21].CN(C)C=O.[ClH:38].C(O)C>CO.C(Cl)(Cl)Cl>[ClH:38].[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[C:3]([O:14][CH2:15][CH2:16][NH:17][CH2:19][CH:20]([C:22]2[CH:23]=[C:24]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH:25]=[CH:26][CH:27]=2)[OH:21])[CH:2]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 11346858N-[3-(2-bromoacetyl)phenyl]methanesulfonamideHCID 186152312-(Dibenzo[b,d]furan-3-yloxy)ethanamineHCID 21887872Ethanol hydrochloride

生成物 1

HCID 18615217(+/-)-N-[3-[2-[2-(dibenzofuran-3-yloxy)ethylamino]-1-hydroxyethyl]phenyl]methanesulfonamide Hydrochloride

試薬・触媒・溶媒 1

HCID 21584188Chloroform methanol溶媒

実験手順

Following the procedures of Example 7, the above-identified compound was synthesized from 224.6 mg of Intermediate 5 and 170 mg of Intermediate 14, with the proviso that the following modification was incorporated. Thus, addition of dimethylformamide was omitted and the purification of the crude product was effected twice by a chromatography (methanol/chloroform of 1/20-1/10). The free amine compound (98.4 mg) was converted into its hydrochloride salt (the above-identified compound) with 1.1 eq. of 0.1 N hydrogenchloride/ethanol, whereupon the solvent was evaporated off under a reduced pressure. To the resulting residue was added diethyl ether and the deposited precipitate was washed diethyl ether and dried under a reduced pressure at 46° C., whereby the above-identified compound was obtained as a powdery product. Rf=0.27 (methanol/chloroform of 1/10).

後処理

  1. customthe purification of the crude product
  2. customwhereupon the solvent was evaporated off under a reduced pressure
  3. additionTo the resulting residue was added diethyl ether
  4. washthe deposited precipitate was washed diethyl ether
  5. customdried under a reduced pressure at 46° C.
  6. customwhereby the above-identified compound was obtained as a powdery product

出典と根拠

ORDレコード
ord-4b1a35ad2cff4e5f8b5c8acc8ce73ad9
出典データセット
uspto-grants-2001_02
特許番号
US06187809B1

反応ノート

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