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

HRID 17377
ノート
印刷プレビュー

反応式

HRID 17377 の反応式
[C:1]([C:3]1[C:8]2[N:9]=[C:10]([C:12]([N:14]([O:16][CH3:17])[CH3:15])=[O:13])[O:11][C:7]=2[C:6](F)=[C:5]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:4]=1[CH3:25])#[N:2].C(N(CC)CC)C.[CH3:33][N:34]([CH3:40])[C@H:35]1[CH2:39][CH2:38][NH:37][CH2:36]1.C(OCC)(=O)C>CS(C)=O.[Cl-].[Na+].O>[C:1]([C:3]1[C:8]2[N:9]=[C:10]([C:12]([N:14]([O:16][CH3:17])[CH3:15])=[O:13])[O:11][C:7]=2[C:6]([N:37]2[CH2:38][CH2:39][C@H:35]([N:34]([CH3:40])[CH3:33])[CH2:36]2)=[C:5]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:4]=1[CH3:25])#[N:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 866308444-Cyano-7-fluoro-N-methoxy-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide

生成物 1

HCID 866308434-Cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-N-methoxy-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide収率 32%

試薬・触媒・溶媒

2
HCID 679Dimethyl Sulfoxide溶媒2 回HCID 57417360Sodium chloride; water溶媒

反応条件

温度
150 °C

実験手順

4-Cyano-7-fluoro-N-methoxy-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide (I-115) (200 mg, 0.59 mmol) was dissolved in dimethyl sulfoxide (10 ml), and at room temperature, triethylamine (99 μl, 0.71 mmol) was added. Next, the solution was heated at 150° C., and a solution of (3S)-3-(dimethylamino)pyrrolidine (90 μl, 0.71 mmol) dissolved in dimethyl sulfoxide (2 ml) was added all at a time, followed by further stirring for 1.5 hours. The mixture liquid was cooled to room temperature, then this was fractionated with ethyl acetate and saturated brine. The aqueous layer was separated, this was extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=94:6) to obtain the entitled compound (81 mg, 32%) as a brown amorphous substance.

後処理

  1. additionwas added all at a time
  2. temperatureThe mixture liquid was cooled to room temperature
  3. customThe aqueous layer was separated
  4. extractionthis was extracted twice with ethyl acetate
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe insoluble matter was separated by filtration
  8. customthe solvent was evaporated away
  9. customthe resulting residue was purified by preparative TLC (eluent, chloroform:methanol=94:6)

出典と根拠

ORDレコード
ord-a52a6c40149e41aca560ea978f27c651
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07737166B2

反応ノート

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