8-Amino-2-iodo-1-methyl-4,5-dihydro-1H-1,7,9-triaza-cyclopenta[a]naphthalene-3-carboxylic acid ethyl ester → 8-Amino-1-methyl-4,5-dihydro-1H-1,7,9-triaza-cyclopenta[a]naphthalene-3-carboxylic acid ethyl ester

HRID 222130

반응식

HRID 222130 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:10]2[CH2:11][CH2:12][C:13]3[C:18]([C:9]=2[N:8]([CH3:20])[C:7]=1I)=[N:17][C:16]([NH2:19])=[N:15][CH:14]=3)=[O:5])[CH3:2].C(O[Na])=O>CN(C=O)C.ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:3][C:4]([C:6]1[C:10]2[CH2:11][CH2:12][C:13]3[C:18]([C:9]=2[N:8]([CH3:20])[CH:7]=1)=[N:17][C:16]([NH2:19])=[N:15][CH:14]=3)=[O:5])[CH3:2]

참가 물질

6

반응물 2

HCID 687058158-Amino-2-iodo-1-methyl-4,5-dihydro-1H-1,7,9-triaza-cyclopenta[a]naphthalene-3-carboxylic acid ethyl esterHCID 178526064HCID 178526064, 화합물

생성물 1

HCID 687069418-Amino-1-methyl-4,5-dihydro-1H-1,7,9-triaza-cyclopenta[a]naphthalene-3-carboxylic acid ethyl ester수율 83%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

반응 조건

온도
100 °C

실험 절차

To a solution of 8-amino-2-iodo-1-methyl-4,5-dihydro-1H-1,7,9-triaza-cyclopenta[a]naphthalene-3-carboxylic acid ethyl ester N1 (0.62 mmol) in DMF (5 mL) and under argon, HCOONa (1.4 mmol) and Pd(Ph3P)4 (0.04 mmol) were added and the mixture was heated at 100° C. for 4 h. The mixture was cooled to rt, diluted with dichloromethane and washed with water. The organic phase was dried (Na2SO4) and evaporated to dryness. Chromatography on silica gel (eluant: AcOEt/hexane 1:1) afforded the title compound (83% yield). ESI (+) MS: m/z 273 (MH+). 1H NMR: 1.32 (t, J=7.07, 3H), 2.70 (t, J=7.70, 2H), 2.90 (t, J=7.70, 2H), 4.18 (s, 3H), 4.25 (q, J=7.07, 2H), 6.35 (bs, 2H), 7.73 (s, 1H), 8.01 (s, 1H).

후처리

  1. temperatureThe mixture was cooled to rt
  2. washwashed with water
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customevaporated to dryness

출처 및 근거

ORD 기록
ord-963cb869411d4090bc806649c394e342
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207180B2

연결된 노트

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