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Triethylamine → 2-Amino-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17444
ノート
印刷プレビュー

反応式

HRID 17444 の反応式
[NH2:1][C:2]1[O:3][C:4]2[C:5](=[C:7]([C:19]#[N:20])[C:8]([CH3:18])=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:10]=2F)[N:6]=1.[CH3:21][N:22]([CH3:28])[C@H:23]1[CH2:27][CH2:26][NH:25][CH2:24]1.C(N(CC)CC)C.C(OCC)(=O)C>CS(C)=O.[Cl-].[Na+].O>[NH2:1][C:2]1[O:3][C:4]2[C:5](=[C:7]([C:19]#[N:20])[C:8]([CH3:18])=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:10]=2[N:25]2[CH2:26][CH2:27][C@H:23]([N:22]([CH3:28])[CH3:21])[CH2:24]2)[N:6]=1
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 685859852-Amino-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

生成物 1

HCID 529457382-Amino-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile収率 30%

試薬・触媒・溶媒 2

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

反応条件

温度
150 °C

実験手順

2-Amino-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-172) (200 mg, 0.75 mmol), (3S)-3-(dimethylamino)pyrrolidine (190 μl, 1.50 mmol) and triethylamine (209 μl, 1.50 mmol) were dissolved in dimethyl sulfoxide (4 ml), and the mixture was heated in a sealed tube at 150° C. for 4 hours. After cooling to room temperature, the reaction liquid was fractionated with ethyl acetate and saturated brine. The aqueous layer was separated, and 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, and the solvent was evaporated away under reduced pressure. The solvent was evaporated away, and the resulting residue was purified by preparative TLC (eluent; 7 N ammonia-containing methanol solution:chloroform=8:92) to obtain the entitled compound (81 mg, 30%) as a roughly-purified product. This was further recrystallized from ethyl acetate-hexane to obtain a brown solid (62 mg).

後処理

  1. temperatureAfter cooling to room temperature
  2. customthe reaction liquid
  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 under reduced pressure
  9. customThe solvent was evaporated away
  10. customthe resulting residue was purified by preparative TLC (eluent; 7 N ammonia-containing methanol solution:chloroform=8:92)

出典と根拠

ORDレコード
ord-6cbc8851b45e4548909aa0af8b4c813e
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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