Ammonia → HCID 25119994, 화합물

HRID 714934노트

반응식

HRID 714934 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[O:10][C:11]([C:22]([OH:24])=O)=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[N:13]=1.O.OC1C2N=N[NH:32]C=2C=CC=1.N.O1CCOCC1.CN(C)CCCN=C=NCC>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[O:10][C:11]([C:22]([NH2:32])=[O:24])=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[N:13]=1

참가 물질

7

반응물 5

HCID 222Ammonia2회HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide2회HCID 312751,4-Dioxane2회HCID 59587418HCID 59587418, 화합물HCID 178526939HCID 178526939, 화합물2회

생성물 1

HCID 25119994HCID 25119994, 화합물수율 69%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-(2,6-difluorophenyl)-4-(4-methoxyphenyl)oxazole-5-carboxylic acid (0.026 g, 0.08 mmol) and hydroxybenzotriazole monohydrate (0.012 g, 0.08 mmol) in DMF (3 mL) was added 0.5M ammonia in dioxane (0.471 mL, 0.24 mmol) and the reaction mixture stirred at room temperature for 10 minutes. 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide (0.015 g, 0.08 mmol) was then added and the resulting reaction mixture stirred at room temperature overnight. After a further addition of hydroxybenzotriazole monohydrate (0.008 g, 0.05 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide (0.010 g, 0.05 mmol) and 0.5M ammonia in dioxane (0.315 mL, 0.1116 mmol) the reaction mixture was stirred at room temperature for 4 hours. The solvent was evaporated in vacuo, and the residue was partitioned between DCM (10 mL) and water (10 mL). The organic phase was washed with water and brine, dried over MgSO4 and the solvent removed in vacuo. The residue was purified by preparative HPLC to afford 2-(2,6-difluorophenyl)-4-(4-methoxyphenyl)oxazole-5-carboxamide (0.018 g, 0.05 mmol, 69%) as a white solid. 1H NMR (CD3OD) δ 3.88 (3H, s), 7.03 (2H, d), 7.25 (2H, t), 7.68 (1H, m), 8.21 (2H, d). LCMS (2) Rt: 2.80; m/z (ES+) 331.

후처리

  1. customthe resulting reaction mixture
  2. stirringstirred at room temperature overnight
  3. stirringwas stirred at room temperature for 4 hours
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was partitioned between DCM (10 mL) and water (10 mL)
  6. washThe organic phase was washed with water and brine
  7. dry with materialdried over MgSO4
  8. customthe solvent removed in vacuo
  9. customThe residue was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-a7ed9abd2e0943d58a769b2045953aa1
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187465B2

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