Dimethylformamide → n-(2-Aminophenyl)-6-(4-(2-(((5-fluoro-2-oxoindolin-3-ylidene)hydrazono)-methyl)-3,5-dimethyl-1h-pyrrole-4-carboxamido)butylamino)nicotinamide

HRID 1695037노트

반응식

HRID 1695037 반응식
[F:1][C:2]1[CH:3]=[C:4]2C(=[CH:9][CH:10]=1)NC(=O)[C:5]2=[N:12][N:13]=CC1(C)CC(C)(C(O)=O)CN1.Cl.C(N=C=NCCCN(C)C)C.[OH:37][C:38]1C2N=NNC=2[CH:41]=[CH:40][CH:39]=1.C([N:49]([CH2:52][CH3:53])[CH2:50][CH3:51])C.[NH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][C:56]=1[NH:61][C:62](=[O:75])[C:63]1[CH:68]=[CH:67][C:66]([NH:69][CH2:70][CH2:71][CH2:72][CH2:73][NH2:74])=[N:65][CH:64]=1.[CH3:76][N:77]([CH:79]=[O:80])C>[Cl-].[Na+].O>[NH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][C:56]=1[NH:61][C:62](=[O:75])[C:63]1[CH:68]=[CH:67][C:66]([NH:69][CH2:70][CH2:71][CH2:72][CH2:73][NH:74][C:38]([C:39]2[C:40]([CH3:41])=[C:52]([CH:53]=[N:13][N:12]=[C:5]3[C:4]4[C:76](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=4)[NH:77][C:79]3=[O:80])[NH:49][C:50]=2[CH3:51])=[O:37])=[N:65][CH:64]=1

참가 물질

8

반응물 6

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57993720N-(2-aminophenyl)-6-(4-aminobutylamino)nicotinamideHCID 1372525122-(((5-Fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)-2,4-dimethyl-1H-pyrrole-4-carboxylic acidHCID 178418300HCID 178418300, 화합물

생성물 1

HCID 136593930n-(2-Aminophenyl)-6-(4-(2-(((5-fluoro-2-oxoindolin-3-ylidene)hydrazono)-methyl)-3,5-dimethyl-1h-pyrrole-4-carboxamido)butylamino)nicotinamide수율 73%

시약·촉매·용매 1

HCID 57417360Sodium chloride; water용매

실험 절차

2-(((5-Fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)-2,4-dimethyl-1H-pyrrole-4-carboxylic acid (328 mg, 1 mmol) and 8 ml of DMF were stirred at room temperature while 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (384 mg, 2 mmol), hydroxybenzotriazole (162 mg, 1.2 mmol), triethylamine (404 mg, 4 mmol) and N-(2-aminophenyl)-6-(4-aminobutylamino)nicotinamide (314 mg, 1.05 mmol) were added. The mixture was stirred for 20 hours at room temperature. The mixture was diluted with 400 mL of brine. The solids were collected by vacuum filtration, washed with water and dried under vacuum to give the title compound (444 mg, 73%) as a red solid. 1H NMR (DMSO-d6)δ1.59 (m, 4H, CH2CH2), 2.32 (s, 3H, pyrrole-CH3), 2.43 (s, 3H, pyrrole-CH3), 3.24 (m, 4H, 2×CH2), 4.85 (s, 2H, benzene-NH2), 6.49 (m, 1H), 6.57 (m, 1H), 6.76 (d, J=8.0 Hz, 1H), 6.85 (m, 1H), 6.93 (m, 1H), 7.12 (d, J=8.0 Hz, 1H), 7.20 (m, 2H), 7.67 (s, 1H), 7.89 (d, J=8.0 Hz, 1H), 8.33 (d, J=8.0 Hz, 1H), 8.63 (s, 2H), 9.35 (s, 1H, benzene-NH), 10.70 (s, 1H, indolinone-NH), 11.82 (s, 1H, pyrrole-NH). LC-MS (m/z) 610 (M+1).

후처리

  1. additionwere added
  2. filtrationThe solids were collected by vacuum filtration
  3. washwashed with water
  4. customdried under vacuum

출처 및 근거

ORD 기록
ord-d94c38aec2d14e06bbb91c5b3b2c3376
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158656B2

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