Cysteamine Hydrochloride → (1)Benzothieno(2,3-f)-1,4-thiazepin-5(2H)-one, 3,4-dihydro-9-methoxy-

HRID 1941118ノート

反応式

HRID 1941118 の反応式
Cl[C:2]1[C:3]2[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:4]=2[S:5][C:6]=1[C:7]([O:9]C)=O.ClC1C2C=C(OC)C=CC=2SC=1C(Cl)=O.Cl.[NH2:33][CH2:34][CH2:35][SH:36].C1CCN2C(=NCCC2)CC1>CN(C=O)C.C(OCC)(=O)C.CO>[CH3:16][O:15][C:13]1[CH:12]=[CH:11][C:4]2[S:5][C:6]3[C:7](=[O:9])[NH:33][CH2:34][CH2:35][S:36][C:2]=3[C:3]=2[CH:14]=1

参加物

8

反応物 4

HCID 9082Cysteamine HydrochlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2801561Methyl 3-chloro-5-methoxy-1-benzothiophene-2-carboxylateHCID 101991093-Chloro-5-methoxybenzo[b]thiophene-2-carbonyl chloride

生成物 1

HCID 461195(1)Benzothieno(2,3-f)-1,4-thiazepin-5(2H)-one, 3,4-dihydro-9-methoxy-収率 74%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a room temperature solution of methyl 3-chloro-5-methoxy-benzo[b]thiophene-2-carboxylate (500 mg, 1.95 mmol) [prepared by reaction of the known 3-chloro-5-methoxy-benzo[b]thiophene-2-carbonyl chloride with methanol- [J. Med. Chem., 35:958 (1992)]] in 20 mL of DMF is added cysteamine-HCl (885 mg, 7.79 mmol) followed by DBU (2.33 mL, 15.58 mmol). The reaction mixture is stirred at room temperature for 1.5 hours then warmed to 70° C. The mixture is diluted with ethyl acetate and washed with aqueous HCl, water and brine. The organic layer is dried over MgSO4, filtered and concentrated in vacuo. The crude product is recrystallized from hexane and ethyl acetate to provide 2,3-dihydro-9-methoxy[1]benzothieno[2,3-f]-1,4-thiazepin-5(4H)-one in 74% yield, mp 209°-209.5° C.

後処理

  1. temperaturethen warmed to 70° C
  2. washwashed with aqueous HCl, water and brine
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product is recrystallized from hexane and ethyl acetate

出典と根拠

ORDレコード
ord-f39555394cf64d15a66404b786b79216
出典データセット
uspto-grants-1997_12
特許番号
US05703069

反応ノート

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