Water → (R)-5-bromo-2-(3-(piperidin-1-yl)pyrrolidin-1-yl)benzo[d]thiazole

HRID 1692008ノート

反応式

HRID 1692008 の反応式
Cl[C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:5]=2[N:6]=1.Cl.Cl.[NH:14]1[CH2:18][CH2:17][C@@H:16]([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:15]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Br:11][C:8]1[CH:9]=[CH:10][C:4]2[S:3][C:2]([N:14]3[CH2:18][CH2:17][C@@H:16]([N:19]4[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]4)[CH2:15]3)=[N:6][C:5]=2[CH:7]=1

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 202512695-Bromo-2-chloro-1,3-benzothiazoleHCID 669057171-[(3R)-pyrrolidin-3-yl]piperidine dihydrochloride

生成物 1

HCID 44124704(R)-5-bromo-2-(3-(piperidin-1-yl)pyrrolidin-1-yl)benzo[d]thiazole

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

A stirred mixture of 2-chloro-5-bromobenzothiazole (CAS #824403-26-1, catalog #20284, Daxian Chemical Institute Ltd., #179, 10169 New Hampshire Ave., Silver Spring, Md. 20903, 2.485 g, 0.0100 mole), (R)-1-(pyrrolidin-3-yl)piperidine dihydrochloride (Reference Example 5c, 2.73 g, 0.0120 mole), and potassium carbonate (6.00 g, 0.04438 mole) in N,N-dimethylformamide (15 mL) is heated to 100° C. with an oil bath for 15 hours. The reaction mixture is cooled to room temperature then poured into water (300 mL). The resulting precipitate is collected by filtration and the filter cake is rinsed with water (600 mL). The solid is dissolved in dichloromethane and the solution is dried (MgSO4) and filtered. The filtrate is concentrated under reduced pressure to give a solid that is crystallized from hot ethyl acetate to give (R)-5-bromo-2-(3-(piperidin-1-yl)pyrrolidin-1-yl)benzo[d]thiazole.

後処理

  1. temperatureThe reaction mixture is cooled to room temperature
  2. filtrationThe resulting precipitate is collected by filtration
  3. washthe filter cake is rinsed with water (600 mL)
  4. dissolutionThe solid is dissolved in dichloromethane
  5. dry with materialthe solution is dried (MgSO4)
  6. filtrationfiltered
  7. concentrationThe filtrate is concentrated under reduced pressure
  8. customto give a solid
  9. customthat is crystallized from hot ethyl acetate

出典と根拠

ORDレコード
ord-62d776290dc745f2aaea5bee58af1e1c
出典データセット
uspto-grants-2012_04
特許番号
US08153813B2

反応ノート

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