Lithium Hydroxide → 2-(4-(7-Amino-6-bromo-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetic acid

HRID 2047066ノート

反応式

HRID 2047066 の反応式
C[Si](C)(C)CCOC[N:7](COCC[Si](C)(C)C)[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]4[C:25]([CH:26]=3)=[CH:24][CH:23]=[CH:22][CH:21]=4)=[C:12]2[N:11]=[C:10]([CH:27]2[CH2:32][CH2:31][CH:30]([CH2:33][C:34]([O:36]CC)=[O:35])[CH2:29][CH2:28]2)[C:9]=1[Br:39].C1COCC1.[Li+].[OH-]>O>[NH2:7][C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]4[C:25]([CH:26]=3)=[CH:24][CH:23]=[CH:22][CH:21]=4)=[C:12]2[N:11]=[C:10]([CH:27]2[CH2:28][CH2:29][CH:30]([CH2:33][C:34]([OH:36])=[O:35])[CH2:31][CH2:32]2)[C:9]=1[Br:39]

参加物

5

反応物 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 66733730(4-{7-[Bis-(2-trimethylsilanyl-ethoxymethyl)-amino]-6-bromo-3-quinolin-3-yl-pyrazolo[1,5-a]pyrimidin-5-yl}-cyclohexyl)-acetic acid ethyl ester

生成物 1

HCID 581734442-(4-(7-Amino-6-bromo-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetic acid

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a 20 mL scintillation vial was charged ethyl 2-(4-(7-(bis((2-(trimethylsilyl)ethoxy)-methyl)amino)-6-bromo-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetate (100 mg, 130 μmol) and 2:1 THF:H2O (10 mL). To this solution was added 1N LiOH(aq) (200 μL). The resulting reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo and the resulting residue was dissolved in TFA and stirred at room temperature for 1 hour. This solution was concentrated in vacuo and the residue was dissolved in 3:1 DMSO:MeCN. The crude product was purified via reverse-phase preparatory HPLC to yield 2-(4-(7-amino-6-bromo-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetic acid (m+H=480.1, retention time=3.95 min (isomer 1) and 4.03 min (isomer 2))

後処理

  1. customThe resulting reaction mixture
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionthe resulting residue was dissolved in TFA
  4. stirringstirred at room temperature for 1 hour
  5. concentrationThis solution was concentrated in vacuo
  6. dissolutionthe residue was dissolved in 3:1 DMSO
  7. customThe crude product was purified via reverse-phase preparatory HPLC

出典と根拠

ORDレコード
ord-e69243f2ef5940738ecfefe51a24d010
出典データセット
uspto-grants-2013_11
特許番号
US08591943B2

反応ノート

読み込み中…