Hydrochloric Acid → 7,9-Difluoro-5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5H-6-thia-chrysen-2-ol hydrochloride salt

HRID 1513938ノート

反応式

HRID 1513938 の反応式
[F:1][C:2]1[CH:19]=[C:18]([F:20])[CH:17]=[C:16]2[C:3]=1[S:4][CH:5]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][N:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]3)=[CH:28][CH:27]=1)[C:6]1[C:15]2=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][C:10]([O:21]S(C)(=O)=O)=[CH:11]2.[OH-].[K+].[Cl-:43].[NH4+].Cl.CCOCC>CO.C(Cl)Cl>[ClH:43].[F:1][C:2]1[CH:19]=[C:18]([F:20])[CH:17]=[C:16]2[C:3]=1[S:4][CH:5]([C:26]1[CH:27]=[CH:28][C:29]([O:32][CH2:33][CH2:34][N:35]3[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]3)=[CH:30][CH:31]=1)[C:6]1[C:15]2=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][C:10]([OH:21])=[CH:11]2

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 11273238Methanesulfonic acid 7,9-difluoro-5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5H-6-thia-chrysen-2-yl ester

生成物 1

HCID 670047327,9-Difluoro-5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5H-6-thia-chrysen-2-ol hydrochloride salt収率 99%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

Dissolve methanesulfonic acid 7,9-difluoro-5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5H-6-thia-chrysen-2-yl ester (5.2 g, 9.0 mmol) in methanol (150 mL). Add potassium hydroxide (5.0 g, 90 mmol) and stir at room temperature. After 4 hours pour into saturated aqueous ammonium chloride and extract with methylene chloride. Dry over sodium sulfate, filter and concentrate. Dissolve residue in methylene chloride (90 mL) and add 2M HCl in ether (9 mL, 18 mmol). Concentrate in vacuo to yield 4.8 g (99%) of the title compound. LCMS Rt (0.01% heptafluorobutyric acid:1.0% isopropylalcohol:water is mobile phase A and 0.01% heptafluorobutyric acid:1.0% isopropylalcohol:acetonitrile is mobile phase B; gradient method 15 to 95% B, Purity@254 nm)=3.21 min (100%); mass spectrum (ion spray): m/z=504.3 (M+H). Chiral HPLC: 87%.

後処理

  1. extractionextract with methylene chloride
  2. dry with materialDry over sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate
  5. concentrationConcentrate in vacuo

出典と根拠

ORDレコード
ord-340c9335acb44245b8fc500147bec5d1
出典データセット
uspto-grants-2012_07
特許番号
US08217032B2

反応ノート

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