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llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0

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反応

Trifluoroacetic acid → (S)-3-(3-(4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-1-(2-hydroxyethyl)-4-isopropylimidazolidin-2-one

HRID 539031

印刷プレビュー

反応式

HRID 539031 の反応式

[OH:1][CH2:2][CH2:3][N:4]1[CH2:8][C@H:7]([CH:9]([CH3:11])[CH3:10])[N:6]([C:12]2[CH:17]=[CH:16][N:15]3[N:18]=[CH:19][C:20]([C:21]4[CH:26]=[CH:25][C:24]([C:27]5[N:31]=[CH:30][N:29](COCC[Si](C)(C)C)[N:28]=5)=[CH:23][CH:22]=4)=[C:14]3[N:13]=2)[C:5]1=[O:40].FC(F)(F)C(O)=O.[OH-].[Na+].CO>>[NH:29]1[CH:30]=[N:31][C:27]([C:24]2[CH:23]=[CH:22][C:21]([C:20]3[CH:19]=[N:18][N:15]4[CH:16]=[CH:17][C:12]([N:6]5[C@@H:7]([CH:9]([CH3:11])[CH3:10])[CH2:8][N:4]([CH2:3][CH2:2][OH:1])[C:5]5=[O:40])=[N:13][C:14]=34)=[CH:26][CH:25]=2)=[N:28]1

参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 3

HCID 6422Trifluoroacetic acid2 回

HCID 23721981Sodium hydroxide methanol

HCID 67034260(S)-1-(2-hydroxyethyl)-4-isopropyl-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)imidazolidin-2-one

生成物 1

HCID 178448149(S)-3-(3-(4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-1-(2-hydroxyethyl)-4-isopropylimidazolidin-2-one収率 4.4%

実験手順

To (S)-1-(2-hydroxyethyl)-4-isopropyl-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)imidazolidin-2-one (0.18 g, 0.32 mmol) was added trifluoroacetic acid (5 mL) and the reaction was stirred at ambient temperature for 3 hours. The reaction was concentrated in vacuo and the material purified by reverse preparative HPLC to yield the crude product and the corresponding trifluoroacetate ester. To this material was added 1N NaOH/MeOH and the mixture stirred at ambient temperature for 2 hours. The mixture was concentrated in vacuo. The combined crude product was purified by reverse preparative HPLC to give (S)-3-(3-(4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-1-(2-hydroxyethyl)-4-isopropylimidazolidin-2-one (0.0061 g, 0.014 mmol, 4.4% yield) as the mono TFA salt. LCMS (APCI+) m/z 433 [M+H]+.

後処理

concentrationThe reaction was concentrated in vacuo
customthe material purified by reverse preparative HPLC
customto yield the crude product
stirringthe mixture stirred at ambient temperature for 2 hours
concentrationThe mixture was concentrated in vacuo
customwas purified by reverse preparative HPLC

出典と根拠

ORDレコード: ord-85d3a62cbb0b476ca8957105d21161bb
出典データセット: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08865726B2

反応ノート

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