Diisopropylethylamine → 3-[4-(azetidin-1-ylcarbonyl)phenoxy]-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-n-(1,5-dimethyl-1h-pyrazol-3-yl)benzamide

HRID 20608

반응식

HRID 20608 반응식
CCN(C(C)C)C(C)C.[N:10]1([C:14]([C:16]2[CH:43]=[CH:42][C:19]([O:20][C:21]3[CH:22]=[C:23]([CH:27]=[C:28]([O:30][C@@H:31]([CH3:41])[CH2:32][O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])[CH:29]=3)[C:24](O)=[O:25])=[CH:18][CH:17]=2)=[O:15])[CH2:13][CH2:12][CH2:11]1.[NH2:44][C:45]1[CH:49]=[C:48]([CH3:50])[N:47]([CH3:51])[N:46]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[N:10]1([C:14]([C:16]2[CH:43]=[CH:42][C:19]([O:20][C:21]3[CH:22]=[C:23]([CH:27]=[C:28]([O:30][C@@H:31]([CH3:41])[CH2:32][O:33][Si:34]([C:37]([CH3:38])([CH3:39])[CH3:40])([CH3:36])[CH3:35])[CH:29]=3)[C:24]([NH:44][C:45]3[CH:49]=[C:48]([CH3:50])[N:47]([CH3:51])[N:46]=3)=[O:25])=[CH:18][CH:17]=2)=[O:15])[CH2:11][CH2:12][CH2:13]1

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 70177471,5-dimethyl-1H-pyrazol-3-amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 593468963-[4-(Azetidin-1-ylcarbonyl)phenoxy]-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)benzoic acid

생성물 1

HCID 593469243-[4-(azetidin-1-ylcarbonyl)phenoxy]-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-n-(1,5-dimethyl-1h-pyrazol-3-yl)benzamide

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

DIPEA (517 mg, 3.00 mmol) was added to a solution of 3-[4-(azetidin-1-ylcarbonyl)phenoxy]-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)benzoic acid (364 mg, 0.75 mmol), 3-amino-1,5-dimethylpyrazole (109 mg, 0.90 mmol) and HATU (599 mg, 1.58 mmol) in DMF (3.0 mL) and the mixture stirred for 24 hours. Water (25 mL) was added and the mixture extracted with ethyl acetate (2×25 mL) dried (MgSO4) and reduced to a brown oil. The crude product was purified by chromatography on silica, eluting with ethyl acetate, to give the required product as a clear oil. (232 mg).

후처리

  1. extractionthe mixture extracted with ethyl acetate (2×25 mL)
  2. dry with materialdried (MgSO4)
  3. customThe crude product was purified by chromatography on silica
  4. washeluting with ethyl acetate

출처 및 근거

ORD 기록
ord-77da95266a1440d4ba6ebc2834eee542
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745475B2

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