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

HRID 1695050ノート

反応式

HRID 1695050 の反応式
[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]([OH:21])=O)[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]=[C:57]([Cl:59])[CH:56]=[CH:55][C:54]=1[NH:60][C:61](=[O:72])[C:62]1[CH:67]=[CH:66][C:65]([NH:68][CH2:69][CH2:70][NH2:71])=[N:64][CH:63]=1>[Cl-].[Na+].O.CN(C=O)C>[NH2:52][C:53]1[CH:58]=[C:57]([Cl:59])[CH:56]=[CH:55][C:54]=1[NH:60][C:61](=[O:72])[C:62]1[CH:67]=[CH:66][C:65]([NH:68][CH2:69][CH2:70][NH:71][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:21])=[N:64][CH:63]=1

参加物

8

反応物 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10979489Sunitinib acidHCID 57993741N-(2-amino-4-chlorophenyl)-6-(2-aminoethylamino)nicotinamideHCID 178418300HCID 178418300、化合物

生成物 1

HCID 44538558(z)-n-(2-Amino-4-chlorophenyl)-6-(2-(2-((5-fluoro-2-oxoindolin-3-ylidene)-methyl)-3,5-dimethyl-1h-pyrrole-4-carboxamido)ethylamino)nicotinamide収率 76%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

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-amino-4-chlorophenyl)-6-(2-aminoethylamino)nicotinamide (321 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 (446 mg, 76%) as a yellow solid. LC-MS (m/z) 588 (M+1).

後処理

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

出典と根拠

ORDレコード
ord-4e1d34f76f74478ab4f16b792466f8c8
出典データセット
uspto-grants-2012_04
特許番号
US08158656B2

反応ノート

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