Methyl iodide → 5-cyclopropyl-6-[(3-hydroxypropyl)(methylsulfonyl)amino]-2-(4-methoxyphenyl)-N-methyl-2H-indazole-3-carboxamide

HRID 1037545노트

반응식

HRID 1037545 반응식
[CH:1]1([C:4]2[C:12]([N:13]([CH2:18][CH2:19][CH2:20][OH:21])[S:14]([CH3:17])(=[O:16])=[O:15])=[CH:11][C:10]3[C:6](=[C:7]([C:29]([NH:31][CH3:32])=[O:30])[N:8]([C:22]4[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=4)[N:9]=3)[CH:5]=2)[CH2:3][CH2:2]1.[C:33](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[CH:1]1([C:4]2[C:12]([N:13]([CH2:18][CH2:19][CH2:20][OH:21])[S:14]([CH3:17])(=[O:15])=[O:16])=[CH:11][C:10]3[C:6](=[C:7]([C:29]([NH:31][CH3:32])=[O:30])[N:8]([C:22]4[CH:23]=[CH:24][C:25]([O:28][CH3:33])=[CH:26][CH:27]=4)[N:9]=3)[CH:5]=2)[CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 675170055-cyclopropyl-2-(4-hydroxyphenyl)-6-[(3-hydroxypropyl)(methylsulfonyl)amino]-N-methyl-2H-indazole-3-carboxamide

생성물 1

HCID 569632575-cyclopropyl-6-[(3-hydroxypropyl)(methylsulfonyl)amino]-2-(4-methoxyphenyl)-N-methyl-2H-indazole-3-carboxamide수율 65%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

To a suspension of compound (ii) (3 mg, 0.007 mmol) and potassium carbonate (3 mg, 0.022 mmol) in DMF (0.25 mL) was added iodomethane (3 μL, 0.048 mmol) and the reaction was stirred at 60° C. for 45 min. The mixture was concentrated to dryness and the residue was purified by reverse phase flash column chromatography eluting with ACN/water (5-100%) to afford Compound (55) as a white solid (2 mg, 65%). ESI-MS m/z calculated for [M+H]+: 473.2; found: 473.2; 1H NMR (400 MHz, Acetone) δ 7.86 (d, J=0.5 Hz, 1H), 7.64 (brs, 1H), 7.62-7.56 (m, 2H), 7.42 (s, 1H), 7.14-7.06 (m, 2H), 3.99-3.85 (m, 5H), 3.71-3.62 (m, 2H), 3.59 (t, J=5.2 Hz, 1H), 3.18 (s, 3H), 2.96 (d, J=4.7 Hz, 3H), 2.52-2.42 (m, 1H), 1.91-1.73 (m, 2H), 1.11-0.94 (m, 3H), 0.64-0.53 (m, 1H).

후처리

  1. concentrationThe mixture was concentrated to dryness
  2. customthe residue was purified by reverse phase flash column chromatography
  3. washeluting with ACN/water (5-100%)

출처 및 근거

ORD 기록
ord-5b8283919d0147918d3f1f8ad0e26571
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546389B2

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