Triethylamine → 4-(3,6-Dimethyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-2-methyl-benzonitrile

HRID 220957노트

반응식

HRID 220957 반응식
CC1[O:11][C:10]2[C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3NCCC=2N=1.S(Cl)(Cl)=O.[CH3:20][N:21]1[C:30]2[NH:29][C:28]3[CH:31]=[C:32]([CH3:35])[CH:33]=[CH:34][C:27]=3[NH:26][CH2:25][C:24]=2[CH:23]=[N:22]1.C([N:38]([CH2:41][CH3:42])CC)C>C1(C)C=CC=CC=1.ClCCl>[CH3:20][N:21]1[C:30]2[NH:29][C:28]3[CH:31]=[C:32]([CH3:35])[CH:33]=[CH:34][C:27]=3[N:26]([C:10]([C:9]3[CH:12]=[CH:13][C:42]([C:41]#[N:38])=[C:15]([CH3:14])[CH:8]=3)=[O:11])[CH2:25][C:24]=2[CH:23]=[N:22]1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 231123652-methyl-5,6-dihydro-4H-benzo[b]oxazolo[5,4-d]azepineHCID 1357360353,6-Dimethyl-3,4,9,10-tetrahydro-2,3,4,9-tetraaza-benzo[f]azulene

생성물 1

HCID 1357360404-(3,6-Dimethyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-2-methyl-benzonitrile수율 85%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6344Dichloromethane용매

실험 절차

A mixture of 4-cyano-3-methyl-benzoic acid from Example E6 (753 mg, 4.7 mmol) and thionyl chloride (1.02 ml, 14.0 mmol) in toluene (50 ml) was heated at reflux for 2 h. After cooling at room temperature, solvents were re-moved in vacuo and azeotroped with toluene. The residue was redissolved in dichloromethane (45 ml) and a solution of 3,6-dimethyl-3,4,9,10-tetrahydro-2,3,4,9-tetraaza-benzo[f]azulene from Example E2 (11.0 g, 4.7 mmol) in dichloromethane (5 ml) and triethylamine (1.3 ml, 9.3 mmol) was added slowly. The mixture was stirred at room temperature for 20 h, washed with brine, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel through an isolute (eluant; EtOAc) to yield the title compound (1.42 g, 85%).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. customazeotroped with toluene
  4. dissolutionThe residue was redissolved in dichloromethane (45 ml)
  5. washwashed with brine
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography on silica gel through an isolute (eluant; EtOAc)

출처 및 근거

ORD 기록
ord-3ca72dc839004bcdba630ed3dd0dc1a2
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202858B2

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