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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Ammonium formate → 3-[(4-Methyl-5-oxo-2,3,4,5-tetrahydro-1,4-benzoxazepin-8-yl)oxy]-N-(1-methyl-1H-pyrazol-3-yl)-5-[(3S)-tetrahydrofuran-3-yloxy]benzamide

HRID 548714
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HRID 548714 반응식
Cl[C:2]1[C:12]2[O:11][CH2:10][CH2:9][N:8]([CH3:13])[C:7](=[O:14])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:15][C:16]1[CH:17]=[C:18]([CH:28]=[C:29]([O:31][C@H:32]2[CH2:36][CH2:35][O:34][CH2:33]2)[CH:30]=1)[C:19]([NH:21][C:22]1[CH:26]=[CH:25][N:24]([CH3:27])[N:23]=1)=[O:20].C([O-])=O.[NH4+]>C(O)C.[Pd]>[CH3:13][N:8]1[C:7](=[O:14])[C:6]2[CH:5]=[CH:4][C:3]([O:15][C:16]3[CH:17]=[C:18]([CH:28]=[C:29]([O:31][C@H:32]4[CH2:36][CH2:35][O:34][CH2:33]4)[CH:30]=3)[C:19]([NH:21][C:22]3[CH:26]=[CH:25][N:24]([CH3:27])[N:23]=3)=[O:20])=[CH:2][C:12]=2[O:11][CH2:10][CH2:9]1
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참가 물질

5

반응물 2

HCID 2723923Ammonium formate2회HCID 159495913-[(9-Chloro-4-methyl-5-oxo-2,3,4,5-tetrahydro-1,4-benzoxazepin-8-yl)oxy]-N-(1-methyl-1H-pyrazol-3-yl)-5-[(3S)-tetrahydrofuran-3-yloxy]benzamide

생성물 1

HCID 159495923-[(4-Methyl-5-oxo-2,3,4,5-tetrahydro-1,4-benzoxazepin-8-yl)oxy]-N-(1-methyl-1H-pyrazol-3-yl)-5-[(3S)-tetrahydrofuran-3-yloxy]benzamide수율 68.5%

시약·촉매·용매 2

HCID 23938Palladium
촉매
HCID 702Ethanol용매

실험 절차

3-[(9-Chloro-4-methyl-5-oxo-2,3,4,5-tetrahydro-1,4-benzoxazepin-8-yl)oxy]-N-(1-methyl-1H-pyrazol-3-yl)-5-[(3S)-tetrahydrofuran-3-yloxy]benzamide (150 mg, 0.29 mmol) was dissolved in ethanol (5 mL) and ammonium formate (147 mg, 2.33 mmol) was added in one portion. The reaction was blanketed with argon and 10% palladium on charcoal (10 mg) was added. The mixture was heated to 140° C. for a total of 55 minutes in a Smith Creator microwave reactor after which time a further 100 mgs of ammonium formate and 10 mgs of catalyst were added and the suspension heated for a further hour. The catalyst was filtered off and the volatiles removed in vacuo to give the crude product as a colourless oil. This residue was purified by reverse phase preparative HPLC, eluting with 5-95% acetoniltrile in water (+0.2% TFA), to give the title compound as a colourless foam (95 mg). 1H NMR δ (CDCl3): 2.12-2.19 (1H, m), 2.23-2.32 (1H, m), 3.23 (3H, s), 3.59 (2H, t), 3.88-3.91 (4H, m), 4.01 (3H, m), 4.42 (2H, t), 5.15-5.17 (1H, m), 6.61 (5H, d), 6.78-6.79 (1H, m), 6.80 (1H, t), 7.02 (1H, d), 7.33-7.36 (2H, m), 7.38-7.40 (1H, m), 7.85 (1H, d), 10.58 (1H, s); m/z 479 (M+H)+.

후처리

  1. additionwas added
  2. additionwere added
  3. temperaturethe suspension heated for a further hour
  4. filtrationThe catalyst was filtered off
  5. customthe volatiles removed in vacuo
  6. customto give the crude product as a colourless oil
  7. customThis residue was purified by reverse phase preparative HPLC
  8. washeluting with 5-95%

출처 및 근거

ORD 기록
ord-bc0c7922d3b44bedb0216246adef797b
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07943607B2

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