Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamate → 1,1-dimethylethyl 7-(2-{[(methyloxy)carbonyl]amino}-1H-imidazo[4,5-b]pyridin-6-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

HRID 241234ノート

反応式

HRID 241234 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[CH:11][C:12]3[O:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14][C:13]=3[CH:26]=2)[CH:5]=[N:6][C:7]=1[NH2:8].[CH3:27][O:28][C:29]([NH:31][C:32](=NC(OC)=O)SC)=[O:30]>C(O)(=O)C>[CH3:27][O:28][C:29]([NH:31][C:32]1[NH:1][C:2]2[C:7]([N:8]=1)=[N:6][CH:5]=[C:4]([C:9]1[CH:10]=[CH:11][C:12]3[O:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])[CH2:14][C:13]=3[CH:26]=1)[CH:3]=2)=[O:30]

参加物

4

反応物 2

HCID 98708Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamateHCID 668202021,1-dimethylethyl 7-(5,6-diaminopyridin-3-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

生成物 1

HCID 668202411,1-dimethylethyl 7-(2-{[(methyloxy)carbonyl]amino}-1H-imidazo[4,5-b]pyridin-6-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate収率 84.5%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
65 °C

実験手順

To a solution of 1,1-dimethylethyl 7-(5,6-diaminopyridin-3-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (0.51 g, 1.4 mmol) in acetic acid (5 mL) was added 1,3-bis(methoxycarbonyl)-2-methyl-2-thiopseudourea (0.3 g, 1.4 mmol). The reaction mixture was heated 65° C. for 18 h and then concentrated. The resulting residue was suspended in water and basified with portion wise addition of solid sodium bicarbonate. After complete neutralization of the aqueous mixture the insoluble solid was collected by filtration and washed with water then 50% ethyl acetate in hexanes and the filter cake dried to give 1,1-dimethylethyl 7-(2-{[(methyloxy)carbonyl]amino}-1H-imidazo[4,5-b]pyridin-6-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (0.52 g, 83% yield), MS (EI) for C22H25N5O5: 440 (MH+).

後処理

  1. concentrationconcentrated
  2. additionThe resulting residue was suspended in water and basified with portion wise addition of solid sodium bicarbonate
  3. filtrationAfter complete neutralization of the aqueous mixture the insoluble solid was collected by filtration
  4. washwashed with water
  5. dry with material50% ethyl acetate in hexanes and the filter cake dried

出典と根拠

ORDレコード
ord-13b27418e01e4cbbb850254a05d4c1de
出典データセット
uspto-grants-2014_02
特許番号
US08648066B2

反応ノート

読み込み中…