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Potassium Phosphate, Tribasic → 5-(3-(6-(1-pyrrolidinyl)-2-pyridinyl)-1H-indol-5-yl)-1,3,4-thiadiazol-2-amine

HRID 634134
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HRID 634134 반응식
[N:1]1([C:6]2[CH:11]=[CH:10][CH:9]=[C:8](B3OC(C)(C)C(C)(C)O3)[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.I[C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([C:31]3[S:35][C:34]([NH2:36])=[N:33][N:32]=3)[CH:29]=2)[N:24](S(C2C=CC(C)=CC=2)(=O)=O)[CH:23]=1.CC(N)CC1C=CC=CC=1.OP(O)(O)=O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CC(O)C.O>[N:1]1([C:6]2[N:7]=[C:8]([C:22]3[C:30]4[C:25](=[CH:26][CH:27]=[C:28]([C:31]5[S:35][C:34]([NH2:36])=[N:33][N:32]=5)[CH:29]=4)[NH:24][CH:23]=3)[CH:9]=[CH:10][CH:11]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1
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참가 물질

7

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 62885Benzeneethanamine, alpha-methyl-, phosphate (1:1)HCID 457857172-(Pyrrolidin-1-YL)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)pyridineHCID 68328527HCID 68328527, 화합물

생성물 1

HCID 683283905-(3-(6-(1-pyrrolidinyl)-2-pyridinyl)-1H-indol-5-yl)-1,3,4-thiadiazol-2-amine수율 8%

시약·촉매·용매 2

HCID 962Water용매HCID 3776Isopropanol용매

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온도
100 °C

실험 절차

A glass microwave reaction vessel was charged with 2-(pyrrolidin-1-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (46 mg, 0.17 mmol, CombiPhos Catalysts, Inc.) and 5-(3-iodo-1-tosyl-1H-indol-5-yl)-1,3,4-thiadiazol-2-amine (060 g, 0.12 mmol) in 66% IPA in H2O (1 mL) followed by Amphos (4 mg, 6 μmol), potassium phosphate (0.077 g, 0.36 mmol). The mixture was stirred and heated in a Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Uppsala, Sweden) at 100° C. for 10 min. The aqueous layer was removed and the resulting mixture was concentrated in vacuo and purified by preparative HPLC. The product was dissolved in p-dioxane (1 mL) and aq. NaOH (1 M, 0.1 mL) was added. The solution was heated in a microwave at 100° C. for 10 min, and purified by preparative HPLC to give 5-(3-(6-(1-pyrrolidinyl)-2-pyridinyl)-1H-indol-5-yl)-1,3,4-thiadiazol-2-amine (3 mg, 8%). MS (ESI, pos. ion) m/z: 364 (M+1). 1H NMR (400 MHz, CD3OD) δ ppm 8.23 (1H, s), 8.00 (1H, s), 7.91 (1H, dd, J=9.0, 7.6 Hz), 7.65 (1H, d, J=8.6 Hz), 7.58 (1H, d, J=8.6 Hz), 7.09 (1H, d, J=7.2 Hz), 6.85 (1H, d, J=9.0 Hz), 3.60-3.68 (4H, m), 2.06-2.14 (4H, m).

후처리

  1. customA glass microwave reaction vessel
  2. customThe aqueous layer was removed
  3. concentrationthe resulting mixture was concentrated in vacuo
  4. custompurified by preparative HPLC
  5. dissolutionThe product was dissolved in p-dioxane (1 mL)
  6. additionaq. NaOH (1 M, 0.1 mL) was added
  7. temperatureThe solution was heated in a microwave at 100° C. for 10 min
  8. custompurified by preparative HPLC

출처 및 근거

ORD 기록
ord-e8894fc6ebd64df8b9a8a227b5fc2fdf
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09321756B2

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