Lithium Hydroxide → HCID 71730558、化合物

HRID 574325

反応式

HRID 574325 の反応式
[C:1]([O:5][C@@H:6]([C:11]1[C:12]([CH3:27])=[N:13][C:14]2[N:15]([N:18]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:20]=2)[C:16]=1Cl)[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].[CH2:28]1[C:32]2([CH2:36][CH2:35][CH2:34][CH2:33]2)[CH2:31][CH2:30][NH:29]1.C(N(CC)C(C)C)(C)C.[OH-].[Li+]>CN1C(=O)CCC1>[C:1]([O:5][C@@H:6]([C:11]1[C:12]([CH3:27])=[N:13][C:14]2[N:15]([N:18]=[C:19]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:20]=2)[C:16]=1[N:29]1[CH2:30][CH2:31][C:32]2([CH2:36][CH2:35][CH2:34][CH2:33]2)[CH2:28]1)[C:7]([OH:9])=[O:8])([CH3:3])([CH3:4])[CH3:2]

参加物

6

反応物 4

HCID 3939Lithium HydroxideHCID 81531DiisopropylethylamineHCID 4189042-Azaspiro(4.4)nonaneHCID 86695058HCID 86695058、化合物

生成物 1

HCID 71730558HCID 71730558、化合物収率 27%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

(S)-methyl 2-(tert-butoxy)-2-(7-chloro-5-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-6-yl)acetate was dissolved in NMP (1 mL) and combined with 2-azaspiro[4.4]nonane (8.72 mg, 0.070 mmol) and N,N-diisopropylethylamine (27 mg, 0.21 mmol). This mixture was stirred at rt for 24 h. A 1M lithium hydroxide solution (0.348 mL, 0.348 mmol) was added to the reaction mixture and it was heated at 50° C. for 4 h to complete the ester hydrolysis. The reaction mixture was concentrated in vacuo and purified by Biotage (4 g column, 0-10% MeOH/CH2Cl2 ramp) to give 11.1 mg (27% yield) of S)-2-(tert-butoxy)-2-(5-methyl-2-phenyl-7-(2-azaspiro[4.4]nonan-2-yl)pyrazolo[1,5-a]pyrimidin-6-yl)acetic (1:1 solvate with NMP) as a yellow waxy solid.

後処理

  1. temperaturewas heated at 50° C. for 4 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompurified by Biotage (4 g column, 0-10% MeOH/CH2Cl2 ramp)

出典と根拠

ORDレコード
ord-9fc06a2025784da2be6d96bcc0732229
出典データセット
uspto-grants-2015_05
特許番号
US09034882B2

関連ノート

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