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Sodium Iodide → 2-Chloro-5-[3-(3-hydroxypropylthio)propoxy]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

HRID 2085639
ノート
印刷プレビュー

反応式

HRID 2085639 の反応式
[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25]Cl)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5].N12CCCN=C1CCCCC2.[I-].[Na+].[SH:40][CH2:41][CH2:42][CH2:43][OH:44]>C(O)CCC.C(OCC)(=O)C>[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][S:40][CH2:41][CH2:42][CH2:43][OH:44])=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 882113-MercaptopropanolHCID 227314912-chloro-5-[3-chloropropoxy]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

生成物 1

HCID 102259552-Chloro-5-[3-(3-hydroxypropylthio)propoxy]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

試薬・触媒・溶媒 2

HCID 263
1-Butanol
溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

To a solution of 2-chloro-5-[3-chloropropoxy]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (0.06 g, Example 3a) and 1,8-diazabicyclo(5.4.0)undec-7-ene (0.07 ml) in 1-butanol (5 ml) was added sodium iodide (0.023 g) and 3-mecaptopropan-1-ol (0.04 ml). The reaction vessel was sealed and the mixture heated at 100° C. for 24 h. The reaction mixture was diluted with ethyl acetate and washed twice with 2M hydrochloric acid, twice with sodium hydrogencarbonate solution and once with brine. The organics were dried (MgSO4) and concentrated under reduced pressure. The residue was purified by NPHPLC (eluting with 0-2% ethanol in dichloromethane) to leave the title compound as a white solid (0.05 g).

後処理

  1. customThe reaction vessel was sealed
  2. washwashed twice with 2M hydrochloric acid, twice with sodium hydrogencarbonate solution and once with brine
  3. dry with materialThe organics were dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by NPHPLC (eluting with 0-2% ethanol in dichloromethane)

出典と根拠

ORDレコード
ord-1376c3d5e6aa4f5f97e6357458a0e950
出典データセット
uspto-grants-2004_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06720452B2

反応ノート

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