Cyclopropanecarbonyl chloride → VA-111913

HRID 220962

반응식

HRID 220962 반응식
[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.Cl.[NH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([N:18]2[CH2:27][C:26]3[CH:25]=[N:24][N:23]([CH3:28])[C:22]=3[NH:21][C:20]3[CH:29]=[C:30]([Cl:33])[CH:31]=[CH:32][C:19]2=3)=[O:17])=[CH:12][C:11]=1[F:34].C1C(N=NC2C(=O)N(C3C=CC(S([O-])(=O)=O)=CC=3)N=C2C([O-])=O)=CC=C(S([O-])(=O)=O)C=1.[Na+].[Na+].[Na+].CCN(C(C)C)C(C)C>ClCCl>[Cl:33][C:30]1[CH:31]=[CH:32][C:19]2[N:18]([C:16]([C:13]3[CH:14]=[CH:15][C:10]([CH2:9][NH:8][C:4]([CH:1]4[CH2:3][CH2:2]4)=[O:5])=[C:11]([F:34])[CH:12]=3)=[O:17])[CH2:27][C:26]3[CH:25]=[N:24][N:23]([CH3:28])[C:22]=3[NH:21][C:20]=2[CH:29]=1

참가 물질

6

반응물 4

HCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 164825Tartrazine2회HCID 136346648(4-Aminomethyl-3-fluoro-phenyl)-(6-chloro-3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulen-9-yl)-methanone Hydrochloride

생성물 1

HCID 135564707VA-111913수율 59%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Cyclopropanecarbonyl chloride (0.045 ml, 0.5 mmol) was added to a solution of (4-aminomethyl-3-fluoro-phenyl)-(6-chloro-3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulen-9-yl)-methanone hydrochloride from Example E102.2 (210 mg, 0.5 mmol) in dichloromethane (40 ml) and DIEA (0.30 ml, 1.7 mmol) at 0° C. The mixture was stirred for 1 h at room temperature then washed with saturated NaHCO3, brine, dried and concentrated in vacuo. The residue was purified by preparative HPLC (eluant; 0.5% 35% ammonia:9.5% methanol:90% dichloro-methane) to give a white powder identified as the title compound (134 mg, 59%).

후처리

  1. customat 0° C
  2. washthen washed with saturated NaHCO3, brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative HPLC (eluant; 0.5% 35% ammonia:9.5% methanol:90% dichloro-methane)
  6. customto give a white powder

출처 및 근거

ORD 기록
ord-1c23eb3d05934fe7b864c3bef6f9f3e0
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202858B2

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