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Acetamidine monohydrochloride → 2-(5-{12-bromo-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaen-4-yl}-3-methyl-1H-1,2,4-triazol-1-yl)ethan-1-ol

HRID 1530624
ノート
印刷プレビュー

反応式

HRID 1530624 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.Cl.[C:18](=[NH:21])([NH2:20])[CH3:19].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)[O:43][C:25]2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=C[C:24]1=2.Cl.[NH:65]([CH2:67]CO)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:67]3[N:65]([CH2:24][CH2:25][OH:43])[N:20]=[C:18]([CH3:19])[N:21]=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 67170Acetamidine monohydrochlorideHCID 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 866714732-Hydrazinylethanol hydrochloride

生成物 1

HCID 683128562-(5-{12-bromo-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaen-4-yl}-3-methyl-1H-1,2,4-triazol-1-yl)ethan-1-ol
収率 800.8%

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

A mixture of 12-bromo-4-iodo-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene (100 mg, 0.256 mmol), acetimidamide hydrochloride (26.5 mg, 0.282 mmol), Pd(OAc)2 (2.9 mg, 0.0129 mmol), Xantphos (14.8 mg, 0.0256 mmol), and TEA (77.6 mg, 0.768 mmol) in DMF (5 mL) was heated at 40° C. under CO (1 atm) for 2 h. After cooling to room temperature, 2-hydrazinylethanol hydrochloride (57.3 mg, 0.512 mmol) and acetic acid (5 mL) were added. The resulting mixture was heated at 80° C. for 0.5 h. The solvent was removed under reduce pressure and the residue was purified by prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min) to afford 2-(5-{12-bromo-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaen-4-yl}-3-methyl-1H-1,2,4-triazol-1-yl)ethan-1-ol (80 mg, 80% yield) as white solid. LCMS (ESI) m/z: 390.1 [M+H+].

後処理

  1. temperatureAfter cooling to room temperature
  2. temperatureThe resulting mixture was heated at 80° C. for 0.5 h
  3. customThe solvent was removed
  4. customthe residue was purified by prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min)

出典と根拠

ORDレコード
ord-c0c6993013984645a4f42a45fad29e40
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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