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3-Methoxypropylamine → 1,2-Dimethylimidazol-5-yl-2-{4-[N-(2-mesylethyl)sulphamoyl]anilino}pyrimidine

HRID 1064313
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HRID 1064313 반응식
COC[CH2:4][CH2:5][NH2:6].[CH3:7][N:8]1[C:12]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([S:26](F)(=[O:28])=[O:27])=[CH:22][CH:21]=3)[N:14]=2)=[CH:11][N:10]=[C:9]1[CH3:30]>CN(C)C1C=CN=CC=1.CN1C(=O)CCC1>[CH3:7][N:8]1[C:12]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([S:26](=[O:28])(=[O:27])[NH:6][CH2:5][CH2:4][S:26]([CH3:23])(=[O:28])=[O:27])=[CH:22][CH:21]=3)[N:14]=2)=[CH:11][N:10]=[C:9]1[CH3:30]
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참가 물질

5

반응물 2

HCID 16723-MethoxypropylamineHCID 222735054-(1,2-Dimethylimidazol-5-yl)-2-(4-(fluorosulphonyl)anilino)pyrimidine

생성물 1

HCID 696657941,2-Dimethylimidazol-5-yl-2-{4-[N-(2-mesylethyl)sulphamoyl]anilino}pyrimidine수율 161.6%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 13387N-methyl-2-pyrrolidone
용매

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온도
100 °C

실험 절차

4-Dimethylaminopyridine (3 mg, 0.025 mmol) and 3-methyoxypropylamine (200 μl, 2 mmol) were added to a solution of 4-(1,2-dimethylimidazol-5-yl)-2-(4-(fluorosulphonyl)anilino)pyrimidine (Method 59; 87 mg, 0.25 mmol) in NMP (1 mL) and the mixture heated at 100° C. for 18 hours. The mixture was allowed to cool to ambient temperature and the solvent removed by evaporation. The residue was purified by preparative LCMS (constant flow of 5% v/v (35% NH3 in MeOH) with a gradient of H2O:CH3CN (5:95 increasing in polarity to 95:5) over 7.5 min) to give the title compound (91 mg, 81%) as a solid. NMR 2.38 (s, 3H), 2.97 (s, 3H), 3.11 (m, 2H), 3.21 (m, 2H), 3.95 (s, 3H), 7.20 (d, 1H), 7.61 (s, 1H), 7.75 (m, 3H), 7.95 (d, 2H), 8.43 (d, 1H), 9.95 (s, 1H); m/z 451.

후처리

  1. temperatureto cool to ambient temperature
  2. customthe solvent removed by evaporation
  3. customThe residue was purified by preparative LCMS (constant flow of 5% v/v (35% NH3 in MeOH) with a gradient of H2O:CH3CN (5:95 increasing in polarity to 95:5) over 7.5 min)

출처 및 근거

ORD 기록
ord-5ba85213a1304ef79839f1ab60ac58a3
출처 데이터셋
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06969714B2

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