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

HRID 1695036노트

반응식

HRID 1695036 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])/[C:5]/2=[CH:12]\[C:13]1[NH:17][C:16]([CH3:18])=[C:15]([C:19](O)=[O:20])[C:14]=1[CH3:22].Cl.C(N=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.[NH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=1[NH:59][C:60](=[O:73])[C:61]1[CH:66]=[CH:65][C:64]([NH:67][CH2:68][CH2:69][CH2:70][CH2:71][NH2:72])=[N:63][CH:62]=1>[Cl-].[Na+].O.CN(C=O)C>[NH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=1[NH:59][C:60](=[O:73])[C:61]1[CH:66]=[CH:65][C:64]([NH:67][CH2:68][CH2:69][CH2:70][CH2:71][NH:72][C:19]([C:15]2[C:14]([CH3:22])=[C:13](/[CH:12]=[C:5]3\[C:6](=[O:11])[NH:7][C:8]4[C:4]\3=[CH:3][C:2]([F:1])=[CH:10][CH:9]=4)[NH:17][C:16]=2[CH3:18])=[O:20])=[N:63][CH:62]=1

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10979489Sunitinib acidHCID 57993720N-(2-aminophenyl)-6-(4-aminobutylamino)nicotinamideHCID 178418300HCID 178418300, 화합물

생성물 1

HCID 44511330(z)-n-(2-Aminophenyl)-6-(4-(2-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-3,5-dimethyl-1h-pyrrole-4-carboxamido)butylamino)nicotinamide수율 77%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

실험 절차

5-(5-Fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (300 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 (447 mg, 77%) as a yellow solid. 1H NMR (DMSO-d6)δ1.59 (m, 4H, CH2CH2), 2.39 (s, 3H, pyrrole-CH3), 2.41 (s, 3H, pyrrole-CH3), 3.25 (m, 4H, 2×CH2), 4.85 (s, 2H, benzene-NH2), 6.49 (m, 1H), 6.57 (m, 1H), 6.75 (d, J=8.0 Hz, 1H), 6.83 (m, 1H), 6.91 (m, 2H), 7.12 (d, J=8.0 Hz, 1H), 7.18 (s, 1H), 7.67˜7.76 (m, 3H), 7.90 (d, J=8.0 Hz, 1H), 8.63 (s, 1H), 9.35 (s, 1H, benzene-NH), 10.88 (s, 1H, indolinone-NH), 13.66 (s, 1H, pyrrole-NH). LC-MS (m/z) 582 (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-0537bda1d61b4c76ae88e05d3161a12a
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158656B2

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