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

HRID 17389

反応式

HRID 17389 の反応式
CS(C)=O.[CH3:5][N:6]([CH3:12])[C@@H:7]1[CH2:11][CH2:10][NH:9][CH2:8]1.[O:13]([CH2:31][CH2:32][N:33]([CH3:55])[C:34]([C:36]1[O:37][C:38]2[C:44](F)=[C:43]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C:42]([CH3:52])=[C:41]([C:53]#[N:54])[C:39]=2[N:40]=1)=[O:35])[Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.C(N(CC)CC)C>[Cl-].[Na+].O>[C:53]([C:41]1[C:39]2[N:40]=[C:36]([C:34]([N:33]([CH2:32][CH2:31][OH:13])[CH3:55])=[O:35])[O:37][C:38]=2[C:44]([N:9]2[CH2:10][CH2:11][C@H:7]([N:6]([CH3:12])[CH3:5])[CH2:8]2)=[C:43]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:42]=1[CH3:52])#[N:54]

参加物

6

反応物 4

HCID 679Dimethyl Sulfoxide2 回HCID 8471TriethylamineHCID 2758521(3R)-(+)-3-(Dimethylamino)pyrrolidineHCID 68584854N-[2-(tert-Butyldiphenylsiloxy)ethyl]-4-cyano-7-fluoro-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide

生成物 1

HCID 685869954-Cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]N-(2-hydroxyethyl)-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide収率 42%

試薬・触媒・溶媒 1

HCID 57417360Sodium chloride; water溶媒

実験手順

Under nitrogen atmosphere, a dimethyl sulfoxide (1 ml) solution of (3R)-3-(dimethylamino)pyrrolidine (76 μl, 598 μmol) was added at 150° C. to a dimethyl sulfoxide (9 ml) solution of N-[2-(tert-butyldiphenylsiloxy)ethyl]-4-cyano-7-fluoro-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide (I-124) (295 mg, 499 μmol) and triethylamine (90 μl, 649 μmol), followed by stirring at the same temperature for 20 minutes. After pooling, 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 (10:1, v/v) gave the entitled compound (93 mg, 42%) as an amorphous substance.

後処理

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

出典と根拠

ORDレコード
ord-d46b01018cac494cac306828d245f9ae
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

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