HCID 2325055, 화합물 → HCID 69201728, 화합물

HRID 2114133노트

반응식

HRID 2114133 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:21])=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([NH:16][CH2:17][CH:18]3[CH2:20][CH2:19]3)=[O:15])=[CH:10][CH:9]=2)[CH:7]=1.[Cl:22][C:23]1[C:24]([C:35](O)=[O:36])=[N:25][C:26]([N:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)=[N:27][CH:28]=1>C1COCC1>[Cl:22][C:23]1[C:24]([C:35]([NH:1][C:2]2[CH:7]=[C:6]([C:8]3[CH:13]=[CH:12][C:11]([C:14]([NH:16][CH2:17][CH:18]4[CH2:20][CH2:19]4)=[O:15])=[CH:10][CH:9]=3)[C:5]([CH3:21])=[CH:4][CH:3]=2)=[O:36])=[N:25][C:26]([N:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)=[N:27][CH:28]=1

참가 물질

4

반응물 2

HCID 2325055HCID 2325055, 화합물HCID 113004885'-amino-N-(cyclopropylmethyl)-2'-methyl-1,1'-biphenyl-4-carboxamide

생성물 1

HCID 69201728HCID 69201728, 화합물수율 36.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

5′-Amino-N-(cyclopropylmethyl)-2′-methyl-1,1′-biphenyl-4-carboxamide (53 mg, 0.189 mmol) and 5-chloro-2-(piperidin-1-yl)pyrimidine-4-carboxylic acid (91.3 mg, 0.38 mmol) were mixed in THF (5 ml) and the mixture shaken in a varian tube for 15 min at room temperature. Carbodiimde resin (500 mg) was added and shaking continued for 48 h. The solution was filtered off and concentrated under vacuum. The residue was chromatographed on a silica gel flash column eluting with ethyl acetate/hexane (1:1) and the solvent evaporated under vacuum to give 5-chloro-N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)-2-(piperidin-1-yl)pyrimidine-4- carboxamide (35 mg). NMR; δH CDCl3 9.50,(1 H, s), 8.40,(1 H, s), 7.83,(2H, d), 7.64,(1H, dd), 7.56,(1H, d), 7.41,(2H, d), 7.27,(1H, d), 6.24,(1H, t), 3.79,(4H, m), 3.35,(2H, m), 2.22,(3H, s), 1.65,(4H, m), 1.08,(1H, m), 0.82,(2H, m), 0.58,(2H, m), 0.30,(2H, m). LCMS: retention time 3.96 min, MH+504.

후처리

  1. stirringshaking
  2. waitcontinued for 48 h
  3. filtrationThe solution was filtered off
  4. concentrationconcentrated under vacuum
  5. customThe residue was chromatographed on a silica gel flash column
  6. washeluting with ethyl acetate/hexane (1:1)
  7. customthe solvent evaporated under vacuum

출처 및 근거

ORD 기록
ord-02ae794d365f49c9957cdf9468ebf058
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07432289B2

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