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

HRID 2114144Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2114144
[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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-784f1f9a755d4fc283e5e99bd51d162c
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07432289B2

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