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1,2-Dichloroethane → N-(3-(1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)-3-fluorobenzamide

HRID 1047533
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HRID 1047533 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.C(=O)(O)[O-].[Na+].[NH:30]1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[N:32]=[C:31]1[C:39]1[C:47]2[C:42](=[CH:43][CH:44]=[C:45]([NH2:48])[CH:46]=2)[N:41]([CH:49]2[CH2:54][CH2:53][CH2:52][CH2:51][O:50]2)[N:40]=1>CN(C=O)C>[NH:32]1[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[N:30]=[C:31]1[C:39]1[C:47]2[C:42](=[CH:43][CH:44]=[C:45]([NH:48][C:5](=[O:7])[C:4]3[CH:8]=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=3)[CH:46]=2)[N:41]([CH:49]2[CH2:54][CH2:53][CH2:52][CH2:51][O:50]2)[N:40]=1
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참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 99683-Fluorobenzoic AcidHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 1363522453-(1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-amine

생성물 1

HCID 136352248N-(3-(1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)-3-fluorobenzamide
수율 60.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

3-Fluorobenzoic acid (10 mg, 0.029 mmol), HOBt (6 mg, 0.044 mmol), EDC (9 mg, 0.045 mmol) and sodium bicarbonate (2.5 mg, 0.029 mmol) were added to a solution of 3-(1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-amine (10 mg, 0.029 mmol) in DMF (6 mL). The reaction mixture was stirred at room temperature for 24 h, and then the solvent was removed in vacuo. Purification by flash chromatography (6% CH3OH/CH2Cl2) afforded the title compound (8 mg) as a off white solid. 1H NMR (400 MHz, CDCl3): δ 8.40 (d, 1H, J=1.6 Hz), 8.15-8.13 (m, 2H), 7.95 (s, 1H), 7.58 (m, 2H), 7.52 (d, 1H, J=9.6 Hz), 7.42-7.36 (m, 2H), 7.21 (m, 2H), 5.69 (dd, 1H, J=2.4 and 9.2 Hz), 3.99 (m, 1H), 3.72 (m, 1H), 2.55 (m, 1H), 2.06 (m, 2H), 1.67 (m, 3H).

후처리

  1. customthe solvent was removed in vacuo
  2. customPurification by flash chromatography (6% CH3OH/CH2Cl2)

출처 및 근거

ORD 기록
ord-dc7df14d8ab646b1a7f77563ddcc8e35
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08569511B2

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