1-Hydroxybenzotriazole → (2-{3-Chloro-5-[(2-cyano-ethyl)-cyclopentyl-carbamoyl]-phenoxy}-ethyl)-pyridin-4-yl-carbamic acid tert-butyl ester

HRID 2268608ノート

反応式

HRID 2268608 の反応式
[C:1]([O:5][C:6]([N:8]([C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1)[CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:18]=[C:19]([Cl:21])[CH:20]=1)[C:15](O)=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH:69]1([NH:74][CH2:75][CH2:76][C:77]#[N:78])[CH2:73][CH2:72][CH2:71][CH2:70]1>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[N:8]([CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([C:15](=[O:16])[N:74]([CH2:75][CH2:76][C:77]#[N:78])[CH:69]2[CH2:73][CH2:72][CH2:71][CH2:70]2)[CH:18]=[C:19]([Cl:21])[CH:20]=1)[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1)([CH3:2])([CH3:3])[CH3:4]

参加物

7

反応物 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27580023-(Cyclopentylamino)propionitrileHCID 18348849Benzoic acid,3-chloro-5-[2-[[(1,1-dimethylethoxy)carbonyl]-4-pyridinylamino]ethoxy]-

生成物 1

HCID 54100150(2-{3-Chloro-5-[(2-cyano-ethyl)-cyclopentyl-carbamoyl]-phenoxy}-ethyl)-pyridin-4-yl-carbamic acid tert-butyl ester収率 146.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of 3-[2-(tert-butoxycarbonyl-pyridin-4-yl-amino)-ethoxy]-5-chloro-benzoic acid (0.100 g), TBTU (0.080 g) and HOBt (0.034 g) in DMF (3 ml) was added DIPEA (0.087 ml) followed by 3-(cyclopentylamino)propionitrile (0.035 g) after 15 min. The reaction mixture was stirred at room temperature for 18 h and then concentrated under reduced pressure. The residue was washed with water and extracted with ethyl acetate. The organic layer was dried with brine and MgSO4, filtered and concentrated to give the title compound (0.190 g) as a brown oil.

後処理

  1. concentrationconcentrated under reduced pressure
  2. washThe residue was washed with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried with brine and MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-95e84b4d8cb940579398e3e7e0895bb2
出典データセット
uspto-grants-2001_12
特許番号
US06326386B1

反応ノート

読み込み中…