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 1530713ノート

反応式

HRID 1530713 の反応式
[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

参加物

8

反応物 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

生成物 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-pentaene収率 373.8%

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 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.

後処理

  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

出典と根拠

ORDレコード
ord-761abcbf4a364caa8b40364379ffc363
出典データセット
uspto-grants-2015_07
特許番号
US09090628B2

反応ノート

読み込み中…