Trifluoroacetic acid → 5-cyclopropyl-N-[3-hydroxy-3-methyl-1-(methylamino)-1-oxobutan-2-yl]-4-[(2S)-1,1,1-trifluoropropan-2-yl]oxypyridine-2-carboxamide

HRID 1480302

반응식

HRID 1480302 반응식
[OH:1][C:2]([CH3:17])([CH3:16])[CH:3]([NH:8][C:9](=[O:15])OC(C)(C)C)[C:4](=[O:7])[NH:5][CH3:6].FC(F)(F)C(O)=O.[CH:25]1([C:28]2[C:29]([O:37][C@@H:38]([CH3:43])[C:39]([F:42])([F:41])[F:40])=[CH:30][C:31](C(O)=O)=[N:32][CH:33]=2)[CH2:27][CH2:26]1>ClCCl>[CH:25]1([C:28]2[C:29]([O:37][C@@H:38]([CH3:43])[C:39]([F:42])([F:40])[F:41])=[CH:30][C:31]([C:9]([NH:8][CH:3]([C:2]([OH:1])([CH3:16])[CH3:17])[C:4]([NH:5][CH3:6])=[O:7])=[O:15])=[N:32][CH:33]=2)[CH2:27][CH2:26]1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 90203567HCID 90203567, 화합물HCID 902045735-Cyclopropyl-4-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-pyridine-2-carboxylic acid

생성물 1

HCID 902044565-cyclopropyl-N-[3-hydroxy-3-methyl-1-(methylamino)-1-oxobutan-2-yl]-4-[(2S)-1,1,1-trifluoropropan-2-yl]oxypyridine-2-carboxamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of tert-butyl N-[2-hydroxy-2-methyl-1-(methylcarbamoyl)propyl]carbamate (example 236a, 760 mg, 1.94 mmol) in dichloromethane (3 ml) was added trifluoroacetic acid (3.00 ml). The reaction mixture was stirred at room temperature overnight. The reaction mixture was evaporated down to dryness and the crude residue was dissolved in toluene. Volatiles were removed in vacuo to afford a white solid which was dried in HV overnight to yield the crude amine (680 mg) as a trifluroacetate salt which was used without any purification. The crude amine salt was used to synthesize the title compound in analogy to Example 112e, using 5-Cyclopropyl-4-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-pyridine-2-carboxylic acid (Example 68a) as starting materials and the title compound was isolated (76 mg, 59%); MS (ESI, m/z): 404.6 (M+H+).

후처리

  1. customThe reaction mixture was evaporated down to dryness
  2. dissolutionthe crude residue was dissolved in toluene
  3. customVolatiles were removed in vacuo
  4. customto afford a white solid which
  5. customwas dried in HV overnight
  6. customto yield the crude amine (680 mg) as a trifluroacetate salt which
  7. customwas used without any purification
  8. customto synthesize the title compound in analogy to Example 112e

출처 및 근거

ORD 기록
ord-4047267547494370a0941503eaa035ce
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409866B2

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