Acetamidine monohydrochloride → 13-Chloro-4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6,12-triazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene

HRID 1530713노트

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HRID 1530713 반응식
[Cl:1][C:2]1[CH:15]=[C:14]2[C:5]([O:6][CH2:7][CH2:8][N:9]3[C:13]2=[N:12][C:11](I)=[CH:10]3)=[CH:4][N:3]=1.Cl.[C:18]([NH2:21])(=[NH:20])[CH3:19].[CH3:22][C:23]1([CH3:63])C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.Cl.[CH:65]([NH:68]N)(C)C>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2].C(O)(=O)C>[Cl:1][C:2]1[CH:15]=[C:14]2[C:5]([O:6][CH2:7][CH2:8][N:9]3[C:13]2=[N:12][C:11]([C:65]2[N:68]([CH:23]([CH3:63])[CH3:22])[N:21]=[C:18]([CH3:19])[N:20]=2)=[CH:10]3)=[CH:4][N:3]=1

참가 물질

8

반응물 4

HCID 67170Acetamidine monohydrochlorideHCID 855731-Isopropylhydrazine hydrochlorideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 5820436210-Chloro-2-iodo-5,6-dihydroimidazo[1,2-d]pyrido[4,3-f][1,4]oxazepine

생성물 1

HCID 8667148313-Chloro-4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6,12-triazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene수율 373.8%

시약·촉매·용매 3

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

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온도
40 °C

실험 절차

A mixture of 13-chloro-4-iodo-9-oxa-3,6,12-triazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene (3.00 g, 8.63 mmol), acetamidine hydrochloride (984 mg, 10.4 mmol), Pd(OAc)2 (194 mg, 0.870 mmol), and Xantphos (998 mg, 1.73 mmol) in DMF (20.0 mL) and TEA (5.0 mL) was heated at 40° C. under CO (1 atm) for 3 hrs. After cooling down, isopropylhydrazine hydrochloride (1.05 g, 9.50 mmol) and acetic acid (20.0 mL) were added. The resulting mixture was heated to 65° C. and stirred at this temperature for 1 hr. At the end of reaction, solvents were removed and the residue was poured into water (2000 mL). The solid was collected and washed with acetone to give the desired product (2.23 g, 73% yield) as a yellow solid. LCMS m/z [M+H]+ 345.2.

후처리

  1. temperatureAfter cooling down
  2. temperatureThe resulting mixture was heated to 65° C.
  3. customAt the end of reaction, solvents
  4. customwere removed
  5. additionthe residue was poured into water (2000 mL)
  6. customThe solid was collected
  7. washwashed with acetone

출처 및 근거

ORD 기록
ord-761abcbf4a364caa8b40364379ffc363
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090628B2

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