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

HRID 2114144노트

반응식

HRID 2114144 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.[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-784f1f9a755d4fc283e5e99bd51d162c
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07432289B2

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