Diisopropylethylamine → (R)-Methyl 6-(2-(tert-butoxycarbonylamino)-3-ethoxypropylamino)-4-cyano-2-(m-tolylamino)nicotinate

HRID 2092810ノート

反応式

HRID 2092810 の反応式
Cl[C:2]1[CH:11]=[C:10]([C:12]#[N:13])[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([NH:14][C:15]2[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=2)[N:3]=1.CCN(C(C)C)C(C)C.[NH2:31][CH2:32][C@@H:33]([NH:38][C:39](=[O:45])[O:40][C:41]([CH3:44])([CH3:43])[CH3:42])[CH2:34][O:35][CH2:36][CH3:37]>CN(C=O)C.CCOC(C)=O>[C:41]([O:40][C:39]([NH:38][C@@H:33]([CH2:34][O:35][CH2:36][CH3:37])[CH2:32][NH:31][C:2]1[CH:11]=[C:10]([C:12]#[N:13])[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([NH:14][C:15]2[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=2)[N:3]=1)=[O:45])([CH3:44])([CH3:43])[CH3:42]

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 58317587Methyl 6-chloro-4-cyano-2-(m-tolylamino)nicotinateHCID 86654723tert-butyl N-((2R)-1-amino-3-ethoxypropan-2-yl)carbamate2 回

生成物 1

HCID 67238775(R)-Methyl 6-(2-(tert-butoxycarbonylamino)-3-ethoxypropylamino)-4-cyano-2-(m-tolylamino)nicotinate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of methyl 6-chloro-4-cyano-2-(m-tolylamino)nicotinate (200 mg, 0.663 mmol) in DMF (5 mL) was added DIPEA (0.232 mL, 1.326 mmol) and (R)-tert-butyl 1-amino-3-ethoxypropan-2-ylcarbamate (174 mg, 0.795 mmol). The reaction mixture was stirred at RT overnight. Additional (R)-tert-butyl 1-amino-3-ethoxypropan-2-ylcarbamate (231.25 mg, 1.061 mmol) was added and the mixture was heated at 65° C. for 1 h. After cooling to RT, the reaction mixture was diluted with EtOAc (30 mL) and washed with water (2×20 mL) and brine (20 mL). The combined organic layers were dried over Na2SO4 and concentrated to thick yellow oil. The crude product was used in the next step without further purification (415 mg). [M+H] calc'd for C25H33N5O5, 484. found, 484.

後処理

  1. temperaturethe mixture was heated at 65° C. for 1 h
  2. temperatureAfter cooling to RT
  3. washwashed with water (2×20 mL) and brine (20 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated to thick yellow oil
  6. customThe crude product was used in the next step without further purification (415 mg)

出典と根拠

ORDレコード
ord-5da44e6648f04ee7b6b863a707357cad
出典データセット
uspto-grants-2013_05
特許番号
US08440689B2

反応ノート

読み込み中…