5-amino-8-chloro-7-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-6-iodo-3,4-dihydroisoquinolin-1(2H)-one → 5-amino-8-chloro-7-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-3,4-dihydroisoquinolin-1(2H)-one

HRID 577602ノート

反応式

HRID 577602 の反応式
[NH2:1][C:2]1[C:11](I)=[C:10]([C:13]2[N:17]([CH3:18])[N:16]=[N:15][C:14]=2[CH3:19])[C:9]([Cl:20])=[C:8]2[C:3]=1[CH2:4][CH2:5][NH:6][C:7]2=[O:21]>[Pd].C(O)(=O)C.CO>[NH2:1][C:2]1[CH:11]=[C:10]([C:13]2[N:17]([CH3:18])[N:16]=[N:15][C:14]=2[CH3:19])[C:9]([Cl:20])=[C:8]2[C:3]=1[CH2:4][CH2:5][NH:6][C:7]2=[O:21]

参加物

5

反応物 1

HCID 867238285-amino-8-chloro-7-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-6-iodo-3,4-dihydroisoquinolin-1(2H)-one

生成物 1

HCID 867238295-amino-8-chloro-7-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-3,4-dihydroisoquinolin-1(2H)-one収率 178.8%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 176Acetic Acid溶媒HCID 887Methanol溶媒

実験手順

Two batches were prepared by the following method: a mixture of 5-amino-8-chloro-7-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-6-iodo-3,4-dihydroisoquinolin-1(2H)-one (293f, 2.9 g, 6.9 mmol each batch) and palladium on carbon (2.9 g) in glacial acetic acid (29 mL) and methanol (290 mL) was stirred under a hydrogen balloon at room temperature overnight. The combined reaction mixtures were filtered through celite, and the filter pad washed with methanol (300 mL). The filtrate was concentrated and the residue purified by silica gel chromatography (eluting with 10:1 dichloromethane/methanol) affording 5-amino-8-chloro-7-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-3,4-dihydroisoquinolin-1(2H)-one (293g, 3.6 g, 65% combined yield) as yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 8.12 (s, 1H), 6.82 (s, 1H), 3.75 (s, 3H), 3.29-3.28 (m, 2H), 2.70-2.67 (m, 2H), 2.07 (s, 3H). MS: 292 [M+1].

後処理

  1. customTwo batches were prepared by the following method
  2. customThe combined reaction mixtures
  3. filtrationwere filtered through celite
  4. washthe filter pad washed with methanol (300 mL)
  5. concentrationThe filtrate was concentrated
  6. customthe residue purified by silica gel chromatography (eluting with 10:1 dichloromethane/methanol)

出典と根拠

ORDレコード
ord-52348bbc034c448696541b48f736140b
出典データセット
uspto-grants-2015_05
特許番号
US09040515B2

反応ノート

読み込み中…