ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
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
  1. ホーム
  2. /反応

Potassium Fluoride → [4-(6-Amino-5-benzothiazol-2-ylpyridin-3-yl)-pyrazol-1-yl]-acetic acid

HRID 1926350
ノート
印刷プレビュー

反応式

HRID 1926350 の反応式
C[O:2][C:3](=[O:11])[CH2:4][N:5]1[CH:9]=[C:8](I)[CH:7]=[N:6]1.[S:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[C:13]1[C:21]1[C:22]([NH2:36])=[N:23][CH:24]=[C:25](B2OC(C)(C)C(C)(C)O2)[CH:26]=1.[F-].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1.O>[NH2:36][C:22]1[N:23]=[CH:24][C:25]([C:8]2[CH:7]=[N:6][N:5]([CH2:4][C:3]([OH:2])=[O:11])[CH:9]=2)=[CH:26][C:21]=1[C:13]1[S:12][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=1
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

6

反応物 3

HCID 522689Potassium FluorideHCID 51072288methyl (4-iodo-1H-pyrazol-1-yl)acetateHCID 574165133-(1,3-Benzothiazol-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine

生成物 1

HCID 67521113[4-(6-Amino-5-benzothiazol-2-ylpyridin-3-yl)-pyrazol-1-yl]-acetic acid

試薬・触媒・溶媒 2

HCID 178418397
HCID 178418397、化合物
触媒
HCID 218864351,4-Dioxane--water (1/1)溶媒

反応条件

温度
85 °C

実験手順

A mixture of (4-iodopyrazol-1-yl)-acetic acid methyl ester (124 mg, 0.467 mmol), 3-benzothiazol-2-yl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridin-2-ylamine (BB8) (150.0 mg, 0.4246 mmol), Pd(PPh3)4 (40 mg, 0.03 mmol), potassium fluoride (74.0 mg, 1.27 mmol) and 4:1 dioxane:water (4:1, 1,4-dioxane:H2O, 6 mL) was heated in the microwave reactor at 85° C. for 30 min. The solution was concentrated in vacuo and dry-loaded onto silica gel for column chromatography. The material was eluted with 2% MeOH/DCM. The fractions containing the product were concentrated in vacuo. The material was redissolved in 1,4-dioxane (5 mL), and 4M HCl in 1,4-dioxane (1 mL) was added. The solution was heated to 50° C. in a sealed tube for 3 h. The solvent was removed in the corrosive pump to afford the title compound as an orange solid. MS (ES+): m/z=352.08 (100) [MH+]. HPLC: tR=2.78 min (ZQ3, polar—5 min).

後処理

  1. concentrationThe solution was concentrated in vacuo and dry-loaded onto silica gel for column chromatography
  2. washThe material was eluted with 2% MeOH/DCM
  3. additionThe fractions containing the product
  4. concentrationwere concentrated in vacuo
  5. dissolutionThe material was redissolved in 1,4-dioxane (5 mL)
  6. addition4M HCl in 1,4-dioxane (1 mL) was added
  7. temperatureThe solution was heated to 50° C. in a sealed tube for 3 h
  8. customThe solvent was removed in the corrosive pump

出典と根拠

ORDレコード
ord-d0de68c390a340ae984f146bd50fb05e
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08178668B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート