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 577602노트

반응식

HRID 577602 반응식
[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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 176Acetic Acid용매HCID 887Methanol용매

실험 절차

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].

후처리

  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)

출처 및 근거

ORD 기록
ord-52348bbc034c448696541b48f736140b
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040515B2

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