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Triethylamine → 4-Cyano-N,N,5-trimethyl-7-[(3S)-3-(methylamino)pyrrolidin-1-yl]-6-(thiophen-2-yl)-1,3-benzoxazole-2-carboxamide

HRID 17598
ノート
印刷プレビュー

反応式

HRID 17598 の反応式
[C:1]([C:3]1[C:8]2[N:9]=[C:10]([C:12]([N:14]([CH3:16])[CH3:15])=[O:13])[O:11][C:7]=2[C:6](F)=[C:5]([C:18]2[S:19][CH:20]=[CH:21][CH:22]=2)[C:4]=1[CH3:23])#[N:2].C(N(CC)CC)C.[CH3:31][NH:32][C@H:33]1[CH2:37][CH2:36][NH:35][CH2:34]1>CS(C)=O>[C:1]([C:3]1[C:8]2[N:9]=[C:10]([C:12]([N:14]([CH3:16])[CH3:15])=[O:13])[O:11][C:7]=2[C:6]([N:35]2[CH2:36][CH2:37][C@H:33]([NH:32][CH3:31])[CH2:34]2)=[C:5]([C:18]2[S:19][CH:20]=[CH:21][CH:22]=2)[C:4]=1[CH3:23])#[N:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 10261057(3S)-(-)-3-(Methylamino)pyrrolidineHCID 685859004-Cyano-7-fluoro-N,N,5-trimethyl-6-(thiophen-2-yl)-1,3-benzoxazole-2-carboxamide

生成物 1

HCID 685849524-Cyano-N,N,5-trimethyl-7-[(3S)-3-(methylamino)pyrrolidin-1-yl]-6-(thiophen-2-yl)-1,3-benzoxazole-2-carboxamide収率 60%

試薬・触媒・溶媒 1

HCID 679
Dimethyl Sulfoxide
溶媒
2 回

実験手順

4-Cyano-7-fluoro-N,N,5-trimethyl-6-(thiophen-2-yl)-1,3-benzoxazole-2-carboxamide (I-308) (160 mg, 0.49 mmol) was dissolved in dimethyl sulfoxide (8.7 ml), and at room temperature, triethylamine (81 μl, 0.58 mmol) was added. The solution was gradually heated from room temperature up to 150° C., and a solution of (3S)-3-(methylamino)pyrrolidine (62 μl, 0.58 mmol) dissolved in dimethyl sulfoxide (1 ml) was added all at a time. After stirred at the same temperature for 50 minutes, this was cooled to room temperature. The solvent was evaporated away under reduced pressure, and the resulting residue was fractionated with chloroform and saturated brine. The aqueous layer was further fractionated twice with chloroform. 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 roughly purified by preparative TLC (eluent, chloroform:7 N ammonia/methanol solution=95:5, v/v), and the roughly-purified product was again purified by preparative TLC (eluent, chloroform:methanol=9:1, v/v) to obtain the entitled compound (119 mg, 60%) as a yellow amorphous substance.

後処理

  1. temperatureThe solution was gradually heated from room temperature up to 150° C.
  2. additionwas added all at a time
  3. customThe solvent was evaporated away under reduced pressure
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe insoluble matter was separated by filtration
  7. customthe solvent was evaporated away
  8. customthe resulting residue was roughly purified by preparative TLC (eluent, chloroform
  9. custom7 N ammonia/methanol solution=95:5, v/v), and the roughly-purified product was again purified by preparative TLC (eluent, chloroform

出典と根拠

ORDレコード
ord-25127ffa1b6142e2b5d7726150419488
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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