2-(Furan-2-yl)quinoline-4-carboxylic acid → N-(4'-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1'-biphenyl-3-yl)-2-fur-2-ylquinoline-4-carboxamide

HRID 2114140ノート

反応式

HRID 2114140 の反応式
[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.[O:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[C:27]1[CH:36]=[C:35]([C:37](O)=[O:38])[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]=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:37]([C:35]4[C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[N:28]=[C:27]([C:23]5[O:22][CH:26]=[CH:25][CH:24]=5)[CH:36]=4)=[O:38])[CH:7]=3)=[CH:9][CH:10]=2)=[O:15])[CH2:20][CH2:19]1

参加物

4

反応物 2

HCID 6976402-(Furan-2-yl)quinoline-4-carboxylic acidHCID 113004885'-amino-N-(cyclopropylmethyl)-2'-methyl-1,1'-biphenyl-4-carboxamide

生成物 1

HCID 69201118N-(4'-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1'-biphenyl-3-yl)-2-fur-2-ylquinoline-4-carboxamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

5′-Amino-N-(cyclopropylmethyl)-2′-methyl-1,1′-biphenyl-4-carboxamide (42 mg, 0.15 mmol) and 2-fur-2-ylquinoline-4-carboxylic acid (95.7 mg, 0.4 mmol) were mixed in THF (5 ml) and the mixture shaken in a varian tube for 30 min at room temperature. Carbodiimde resin (442 mg, 0.5 mmol) was added and shaking continued for 18 h. The solution was filtered off, the resin washed with THF and methanol and the combined filtrate and washings reduced to dryness under vacuum. The residue was dissolved in ethyl acetate, washed with hydrochloric acid (1M) and aqueous sodium hydrogen carbonate. The solvent was evaporated from the organic fraction under vacuum to give N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)-2-fur-2-ylquinoline-4-carboxamide. NMR; δH [2H6]—DMSO 10.85,(1H, s), 8.62,(1H, t), 8.12-8.07,(3H, m), 7.97,(1H, m), 7.94,(2H, d), 7.82,(1H, m), 7.72,(2H, m), 7.63,(1H, m), 7.49-7.45,(3H, m), 7.34,(1H, d), 6.75,(1H, m), 3.16,(2H, t), 2.23,(3H, s), 1.04,(1H, m), 0.43,(2H, m), 0.24,(2H, m). LCMS: retention time 3.69 min, MH+502.

後処理

  1. stirringshaking
  2. waitcontinued for 18 h
  3. filtrationThe solution was filtered off
  4. washthe resin washed with THF and methanol
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with hydrochloric acid (1M) and aqueous sodium hydrogen carbonate
  7. customThe solvent was evaporated from the organic fraction under vacuum

出典と根拠

ORDレコード
ord-015cfa2eb5aa4232b4fb6d9e635a3e29
出典データセット
uspto-grants-2008_10
特許番号
US07432289B2

反応ノート

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