Trifluoroacetic acid → N-(4'-{[(Cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1'-biphenyl-3-yl)trifluoroacetamide

HRID 2114144ノート

反応式

HRID 2114144 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.[F:22][C:23]([F:28])([F:27])[C:24](O)=[O:25]>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:24](=[O:25])[C:23]([F:28])([F:27])[F:22])[CH:7]=3)=[CH:9][CH:10]=2)=[O:15])[CH2:20][CH2:19]1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 113004885'-amino-N-(cyclopropylmethyl)-2'-methyl-1,1'-biphenyl-4-carboxamide

生成物 1

HCID 86595282N-(4'-{[(Cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1'-biphenyl-3-yl)trifluoroacetamide

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 (30 mg, 0.11 mmol) and trifluoroacetic acid (28.5 mg, 0.25 mmol) were mixed in THF (3 ml). Carbodiimde resin (295 mg, 0.31 mmol) was added and shaking continued for 72 h. The reaction was filtered, the resin washed with THF and methanol and the combined filtrate and washings filtered through an SPE (SCX), to give, after evaporation of the solvent under vacuum, N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)trifluoracetamide. NMR; δH [2H6]—DMSO 11.25,(1H, s), 8.62,(1H, t), 7.92,(2H, d), 7.60,(1H, dd), 7.55,(1H, d), 7.43,(2H, d), 7.34,(1H, d), 3.16,(2H, t), 2.21,(3H, s), 1.04,(1H, m), 0.43,(2H, m), 0.24,(2H, m). LCMS: retention time 3.29 min, MH+377.

後処理

  1. filtrationThe reaction was filtered
  2. washthe resin washed with THF and methanol
  3. filtrationthe combined filtrate and washings filtered through an SPE (SCX)
  4. customto give
  5. customafter evaporation of the solvent under vacuum, N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)trifluoracetamide

出典と根拠

ORDレコード
ord-784f1f9a755d4fc283e5e99bd51d162c
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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