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Sodium Bicarbonate → (S)-tert-butyl (1-((3-(6-((3-fluorophenyl)amino)-4-(propylamino)nicotinamido)phenyl)amino)-1-oxopropan-2-yl)(methyl)carbamate

HRID 2284812
ノート
印刷プレビュー

反応式

HRID 2284812 の反応式
[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:17]=[C:16]([NH:18][CH2:19][CH2:20][CH3:21])[C:12]([C:13]([OH:15])=O)=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[NH2:22][C:23]1[CH:24]=[C:25]([NH:29][C:30](=[O:42])[C@@H:31]([N:33]([CH3:41])[C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH3:32])[CH:26]=[CH:27][CH:28]=1.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.C(=O)([O-])O.[Na+]>CN(C)C=O.C(N(CC)C(C)C)(C)C>[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:17]=[C:16]([NH:18][CH2:19][CH2:20][CH3:21])[C:12]([C:13]([NH:22][C:23]3[CH:24]=[C:25]([NH:29][C:30](=[O:42])[C@@H:31]([N:33]([CH3:41])[C:34](=[O:40])[O:35][C:36]([CH3:37])([CH3:39])[CH3:38])[CH3:32])[CH:26]=[CH:27][CH:28]=3)=[O:15])=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 90051717(S)-tert-butyl (1-((3-aminophenyl)amino)-1-oxopropan-2-yl)(methyl)carbamateHCID 900521806-((3-Fluorophenyl)amino)-4-(propylamino)nicotinic acid

生成物 1

HCID 90052372
(S)-tert-butyl (1-((3-(6-((3-fluorophenyl)amino)-4-(propylamino)nicotinamido)phenyl)amino)-1-oxopropan-2-yl)(methyl)carbamate
収率 72.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 81531Diisopropylethylamine溶媒

反応条件

温度
40 °C

実験手順

To a solution of 6-((3-fluorophenyl)amino)-4-(propylamino)nicotinic acid (S16, 87 mg), (S)-tert-butyl (1-((3-aminophenyl)amino)-1-oxopropan-2-yl)(methyl)carbamate (B9, 115 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (115 mg) and 1-hydroxybenzotriazole monohydrate (81 mg) in N,N-dimethylformamide (2 mL), N,N-diisopropylethylamine (157 μL) was added at room temperature, and the mixture was stirred at 40° C. for 15 hours. The reaction mixture was cooled to room temperature, and then saturated aqueous sodium hydrogencarbonate was added to the reaction mixture. The solid matter was taken by filtration, washed with water, and then purified by silica gel column chromatography (eluent, 75 to 35% hexane in ethyl acetate) to obtain (S)-tert-butyl (1-((3-(6-((3-fluorophenyl)amino)-4-(propylamino)nicotinamido)phenyl)amino)-1-oxopropan-2-yl)(methyl)carbamate (S17, 123 mg).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe solid matter was taken by filtration
  3. washwashed with water
  4. custompurified by silica gel column chromatography (eluent, 75 to 35% hexane in ethyl acetate)

出典と根拠

ORDレコード
ord-abfd272ff19245419ccf6e286a1e439c
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09145415B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート