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HOAt → {(S)-1-[4-fluoro-2-(pyridin-3-ylamino)phenylcarbamoyl]propyl}carbamic acid tert-butyl ester

HRID 242969
ノート
印刷プレビュー

反応式

HRID 242969 の反応式
[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[C:5]([NH2:8])=[CH:6][CH:7]=1.[C:16]([O:20][C:21]([NH:23][C@@H:24]([CH2:28][CH3:29])[C:25](O)=[O:26])=[O:22])([CH3:19])([CH3:18])[CH3:17].C1C=NC2N(O)N=NC=2C=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[C:16]([O:20][C:21](=[O:22])[NH:23][C@H:24]([C:25](=[O:26])[NH:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[NH:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)[CH2:28][CH3:29])([CH3:17])([CH3:18])[CH3:19]
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

6

反応物 4

HCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2755934(S)-2-((tert)-Butoxycarbonyl)amino)butanoic acidHCID 584592164-Fluoro-N2-pyridin-3-ylbenzene-1,2-diamine

生成物 1

HCID 68157109{(S)-1-[4-fluoro-2-(pyridin-3-ylamino)phenylcarbamoyl]propyl}carbamic acid tert-butyl ester収率 75%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of 4-fluoro-N2-pyridin-3-ylbenzene-1,2-diamine (0.594 g, 2.9 mmol) in DCM (18 mL) at 0° C. were added (S)-2-tertbutoxycarbonylaminobutyric acid (650 mg, 3.2 mmol), HOAt (440 mg, 3.2 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (610 mg, 3.2 mmol) and the reaction mixture stirred at 0° C. for 2 h. The crude mixture was partitioned between DCM and a saturated aqueous solution of NaHCO3. The organic phase was washed with brine, dried (MgSO4), concentrated in vacuo and the resulting residue purified by column chromatography (Si—PCC, gradient 0-60% EtOAc in cyclohexane) to afford {(S)-1-[4-fluoro-2-(pyridin-3-ylamino)phenylcarbamoyl]propyl}carbamic acid tert-butyl ester (839 mg, 75%). LCMS (Method J): RT 0.69 min [M+H]+ 389.2.

後処理

  1. customThe crude mixture was partitioned between DCM
  2. washThe organic phase was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customthe resulting residue purified by column chromatography (Si—PCC, gradient 0-60% EtOAc in cyclohexane)

出典と根拠

ORDレコード
ord-8aa39074392a4974b5e288b1405134ea
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08653089B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート