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

HRID 1926350
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HRID 1926350 반응식
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
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참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 218864351,4-Dioxane--water (1/1)용매

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온도
85 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d0de68c390a340ae984f146bd50fb05e
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08178668B2

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