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Potassium Carbonate → 5-Cyclopropyl-N-methyl-2-(4-methylphenyl)-6-{(methylsulfonyl)[2-(oxetan-3-yl)ethyl]amino}-2H-indazole-3-carboxamide

HRID 63537
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HRID 63537 반응식
CS(O[CH2:6][CH2:7][CH:8]1[CH2:11][O:10][CH2:9]1)(=O)=O.O1CC(CCO)C1.CS(Cl)(=O)=O.CCN(C(C)C)C(C)C.[CH:33]1([C:36]2[C:44]([NH:45][S:46]([CH3:49])(=[O:48])=[O:47])=[CH:43][C:42]3[C:38](=[C:39]([C:57]([NH:59][CH3:60])=[O:58])[N:40]([C:50]4[CH:55]=[CH:54][C:53]([CH3:56])=[CH:52][CH:51]=4)[N:41]=3)[CH:37]=2)[CH2:35][CH2:34]1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.C(#N)C.CCOC(C)=O>[CH:33]1([C:36]2[C:44]([N:45]([S:46]([CH3:49])(=[O:48])=[O:47])[CH2:6][CH2:7][CH:8]3[CH2:9][O:10][CH2:11]3)=[CH:43][C:42]3[C:38](=[C:39]([C:57]([NH:59][CH3:60])=[O:58])[N:40]([C:50]4[CH:55]=[CH:54][C:53]([CH3:56])=[CH:52][CH:51]=4)[N:41]=3)[CH:37]=2)[CH2:34][CH2:35]1
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참가 물질

10

반응물 6

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 108443452-(Oxetan-3-yl)ethan-1-olHCID 86698999HCID 86698999, 화합물2회HCID 86699000HCID 86699000, 화합물

생성물 1

HCID 71748269
5-Cyclopropyl-N-methyl-2-(4-methylphenyl)-6-{(methylsulfonyl)[2-(oxetan-3-yl)ethyl]amino}-2H-indazole-3-carboxamide
수율 14%

시약·촉매·용매 3

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of 2-(oxetan-3-yl)ethyl methanesulfonate (11 mg, 0.06 mmol, prepared by treating 2-(oxetan-3-yl)ethanol with methanesulfonyl chloride in DCM in the presence of DIPEA) was added 5-cyclopropyl-6-(methanesulfonamido)-N-methyl-2-(p-tolyl)indazole-3-carboxamide (24 mg, 0.06 mmol) followed by potassium carbonate (68 mg, 0.49 mmol). The resultant suspension was heated at 60° C. for 18 h whereupon another portion of (oxetan-3-yl)ethyl methanesulfonate (81 mg, 0.45 mmol) in ACN (2 mL) was added and heating/stirring continued. After 24 h, the reaction mixture was diluted with EtOAc (15 mL) and the organics washed with water (20 mL). The aqueous layer was back-extracted into EtOAc (15 mL) and the combined organics were then washed with brine (10 mL), dried (MgSO4) and the volatiles removed in vacuo. The residue was purified by preparative HPLC eluting with ACN:0.1% formic acid in water (gradient elution, 5% to 30% to 40% to 100%) to give Compound (3) (4 mg, 14%). ESI-MS m/z calculated for [M+H]+: 483.2 found: 483.1. 1H NMR (400 MHz, CD3CN) δ 7.78 (s, 1H), 7.58 (s, 1H), 7.51 (d, J=8.2 Hz, 2H), 7.40 (d, J=7.94 Hz, 2H), 5.63 (brs, 1H), 4.86-4.78 (m, 2H), 4.40-4.33 (m, 2H), 3.70 (t, J=7.94 Hz, 2H), 3.18-3.05 (m, 4H), 2.98 (d, J=5.0 Hz, 3H), 2.51 (s, 3H), 2.47-2.38 (m, 1H), 2.17-1.97 (m, 2H), 1.19-1.03 (m, 3H), 0.72-0.63 (m, 1H).

후처리

  1. additionwas added
  2. washthe organics washed with water (20 mL)
  3. extractionThe aqueous layer was back-extracted into EtOAc (15 mL)
  4. washthe combined organics were then washed with brine (10 mL)
  5. dry with materialdried (MgSO4)
  6. customthe volatiles removed in vacuo
  7. customThe residue was purified by preparative HPLC
  8. washeluting with ACN

출처 및 근거

ORD 기록
ord-8227a37ccf354b5a9a6fff2ccde362d3
출처 데이터셋
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09447080B2

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