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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
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HRID 1530624 반응식
[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
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참가 물질

8

반응물 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

생성물 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
수율 800.8%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 176Acetic Acid용매HCID 6228Dimethylformamide용매

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온도
40 °C

실험 절차

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+].

후처리

  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)

출처 및 근거

ORD 기록
ord-c0c6993013984645a4f42a45fad29e40
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09090628B2

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