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Dimethyl Sulfoxide → 4-cyano-N-[2-(dimethylamino)-2-oxoethyl]-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide

HRID 17391
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HRID 17391 반응식
CS(C)=O.[CH3:5][N:6]([CH3:12])[C@H:7]1[CH2:11][CH2:10][NH:9][CH2:8]1.[C:13]([C:15]1[C:20]2[N:21]=[C:22]([C:24]([N:26]([CH2:28][C:29]([N:31]([CH3:33])[CH3:32])=[O:30])[CH3:27])=[O:25])[O:23][C:19]=2[C:18](F)=[C:17]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:16]=1[CH3:41])#[N:14].C(N(CC)CC)C>[Cl-].[Na+].O>[C:13]([C:15]1[C:20]2[N:21]=[C:22]([C:24]([N:26]([CH2:28][C:29]([N:31]([CH3:33])[CH3:32])=[O:30])[CH3:27])=[O:25])[O:23][C:19]=2[C:18]([N:9]2[CH2:10][CH2:11][C@H:7]([N:6]([CH3:12])[CH3:5])[CH2:8]2)=[C:17]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:16]=1[CH3:41])#[N:14]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 679Dimethyl Sulfoxide2회HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 68585307HCID 68585307, 화합물

생성물 1

HCID 685849564-cyano-N-[2-(dimethylamino)-2-oxoethyl]-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide수율 14.4%

시약·촉매·용매 1

HCID 57417360Sodium chloride; water용매

실험 절차

Under nitrogen atmosphere, a dimethyl sulfoxide (1 ml) solution of (3S)-3-(dimethylamino)pyrrolidine (52 μl, 408 μmol) was added at 150° C. to a dimethyl sulfoxide (6 ml) solution of 4-cyano-N-[2-(dimethylamino)-2-oxoethyl]-7-fluoro-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide (I-125) (134 mg, 340 μmol) and triethylamine (62 μl, 442 μmol), followed by stirring at the same temperature for 50 minutes. After cooling, saturated brine was added to the reaction liquid, and the reaction liquid was extracted with ethyl acetate. Next, the combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography, and the eluate with dichloromethane/methanol (20:1, v/v) gave the entitled compound (24 mg, 14%) as an amorphous substance.

후처리

  1. temperatureAfter cooling
  2. customthe reaction liquid
  3. extractionwas extracted with ethyl acetate
  4. washNext, the combined organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-0bab741dbfa04a6789f2a25b42736215
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07737166B2

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