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Acetamidine → 12-bromo-4-[1-(2-methoxypropyl)-3-methyl-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaene

HRID 1530621
ノート
印刷プレビュー

反応式

HRID 1530621 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]1[N:8]([CH:9]=[C:10](I)[N:11]=1)[CH2:7][CH2:6][O:5]2.[C:17](=[NH:20])([NH2:19])[CH3:18].CC1(C)C2[C:43](=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)[O:42][C:24]2[C:25](P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=C[C:23]1=2.COC(C)[CH2:66][NH:67]N>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2].C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]1[N:8]([CH:9]=[C:10]([C:66]3[N:67]([CH2:23][CH:24]([O:42][CH3:43])[CH3:25])[N:19]=[C:17]([CH3:18])[N:20]=3)[N:11]=1)[CH2:7][CH2:6][O:5]2
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 67171AcetamidineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 582048589-Bromo-2-iodo-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepineHCID 86671471(2-Methoxypropyl)hydrazine

生成物 1

HCID 6831299312-bromo-4-[1-(2-methoxypropyl)-3-methyl-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaene
収率 325%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 176Acetic Acid溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
40 °C

実験手順

To a solution of 12-bromo-4-iodo-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaene (1.0 g, 2.6 mmol) in dry DMF (20 mL) was added hydrochloric acetimidamide (266 mg, 2.81 mmol), Pd(OAc)2 (58 mg, 0.26 mmol), and Xantphos (305 mg, 0.520 mmol). The reaction mixture was stirred at 40° C. for 3 h under carbon monoxide atmosphere. LCMS indicated complete conversion. Acetic acid (40 mL) and hydrochloric (2-methoxypropyl)hydrazine (577 mg, 5.20 mmol) were added, the resultant mixture was stirred at 100° C. for 1 h. After concentration, the residue was purified by silica gel chromatography eluting with DCM/methanol (100:1) to give 12-bromo-4-[1-(2-methoxypropyl)-3-methyl-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaene (707 mg, 65% yield) as white solid. LCMS (ESI) m/z: 418.3 [M+H+].

後処理

  1. concentrationAfter concentration
  2. customthe residue was purified by silica gel chromatography
  3. washeluting with DCM/methanol (100:1)

出典と根拠

ORDレコード
ord-206ad0d57fff456c975f5a33409fc63a
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09090628B2

反応ノート

読み込み中…

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