5'-amino-N-(cyclopropylmethyl)-2'-methyl-1,1'-biphenyl-4-carboxamide → N-(4'-{[(cyclopropylmethyl)amino]carbonyl}-6methyl-1,1'-biphenyl-3-yl)-2-phenylpyrimidine-4-carboxamide

HRID 2114132노트

반응식

HRID 2114132 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.[C:22]1([C:28]2[N:33]=[C:32]([C:34](O)=[O:35])[CH:31]=[CH:30][N:29]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1>[CH:18]1([CH2:17][NH:16][C:14]([C:11]2[CH:12]=[CH:13][C:8]([C:6]3[C:5]([CH3:21])=[CH:4][CH:3]=[C:2]([NH:1][C:34]([C:32]4[CH:31]=[CH:30][N:29]=[C:28]([C:22]5[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=5)[N:33]=4)=[O:35])[CH:7]=3)=[CH:9][CH:10]=2)=[O:15])[CH2:20][CH2:19]1

참가 물질

4

반응물 2

HCID 113004885'-amino-N-(cyclopropylmethyl)-2'-methyl-1,1'-biphenyl-4-carboxamideHCID 217091412-Phenylpyrimidine-4-carboxylic acid

생성물 1

HCID 69204169N-(4'-{[(cyclopropylmethyl)amino]carbonyl}-6methyl-1,1'-biphenyl-3-yl)-2-phenylpyrimidine-4-carboxamide수율 14.9%

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 2-phenylpyrimidine-4-carboxylic acid (99.5 mg, 0.50 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 N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6methyl-1,1′-biphenyl-3-yl)-2-phenylpyrimidine-4-carboxamide (13 mg). NMR; δH CDCl3 9.98,(1H, s), 9.09,(1H, d), 8.50-8.47,(2H, m), 8.08,(1H, d), 7.86,(2H, d), 7.70,(1H, dd), 7.63,(1H, d), 7.56-7.54,(3H, m), 7.45,(2H, d), 7.33,(1H, d), 7.26,(1H, m), 3.36,(2H, m), 2.26,(3H, s), 1.09,(1H, m), 0.58,(2H, m), 0.30,(2H, m). LCMS: retention time 3.88 min, MH+463.

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-083742d3d5ec4f50942fff920d7a1ea4
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07432289B2

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