O-Phenylenediamine → 6-(5-(((5-fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamido)-N-(2-aminophenyl)hexanamide

HRID 251667노트

반응식

HRID 251667 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=[N:12][N:13]=[CH:14][C:15]1[NH:19][C:18]([CH3:20])=[C:17]([C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29](O)=[O:30])=[O:22])[C:16]=1[CH3:32].Cl.C(N=C=NCCCN(C)C)C.O[C:46]1[C:54]2[N:53]=N[NH:51][C:50]=2[CH:49]=[CH:48][CH:47]=1.C(N(CC)CC)C.C1(N)C=CC=CC=1N>[Cl-].[Na+].O.CN(C=O)C>[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=[N:12][N:13]=[CH:14][C:15]1[NH:19][C:18]([CH3:20])=[C:17]([C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([NH:51][C:50]2[CH:49]=[CH:48][CH:47]=[CH:46][C:54]=2[NH2:53])=[O:30])=[O:22])[C:16]=1[CH3:32]

참가 물질

8

반응물 5

HCID 7243O-PhenylenediamineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 1363879516-(5-(((5-fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamido)-hexanoic acidHCID 178418300HCID 178418300, 화합물

생성물 1

HCID 1363879546-(5-(((5-fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamido)-N-(2-aminophenyl)hexanamide수율 81%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

실험 절차

6-(5-(((5-fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamido)-hexanoic acid (441 mg, 1 mmol), and 8 ml of DMF were stirred at room temperature while 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (394 mg, 2 mmol), hydroxy-benzotriazole (162 mg, 1.2 mmol), triethylamine (404 mg, 4 mmol) and o-phenylenediamine (432 mg, 4 mmol) were added. The mixture was stirred for 24 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 (430 mg, 81% yield) as a red solid. 1H NMR (DMSO-d6)δ1.38 (m, 2H, CH2), 1.54 (m, 2H, CH2), 1.62 (m, 2H, CH2), 2.30 (s, 3H, pyrrole-CH3), 2.32 (t, J=8.0 Hz, 2H, CH2CO), 2.41 (s, 3H, pyrrole-CH3), 3.22 (m, 2H, NCH2), 4.82 (s, 2H, benzene-NH2), 6.51 (t, J=8.0 Hz, 1H, Ar—H), 6.69 (d, J=8.0 Hz, 1H, Ar—H), 6.87 (m, 2H, Ar—H), 7.14 (d, J=8.0 Hz, 1H, Ar—H), 7.20 (m, 1H, Ar—H), 7.65 (t, J=4.0 Hz, 1H, CONH), 8.33 (dd, J=4.0 and 8.0 Hz, 1H, Ar—H), 8.63 (s, 1H, vinyl-H), 9.11 (s, 1H, benzene-NH), 10.73 (s, 1H, indolinone-NH), 11.82 (s, 1H, pyrrole-NH). LC-MS (m/z) 532 (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-4ce62858bf064d17b840673ad343e4bc
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863315B2

반응 노트

불러오는 중…