N,N-Dimethylethylenediamine → (1R,2S)-ethyl 1-((2S,4R)-1-((S)-2-(2-methylpyrimidine-5-carboxamido)non-8-enoyl)-4-(3-(benzo[d]thiazol-2-yl)quinoxalin-2-yloxy)pyrrolidine-2-carboxamido)-2-vinylcyclopropanecarboxylate

HRID 238077

反応式

HRID 238077 の反応式
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([O:20][C@H:21]2[CH2:25][NH:24][C@H:23]([C:26]([NH:28][C@:29]3([C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH2:31][C@H:30]3[CH:32]=[CH2:33])=[O:27])[CH2:22]2)=[N:12][C:13]2[C:18]([N:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2.[CH3:39][C:40]1[N:45]=[CH:44][C:43]([C:46]([NH:48][C@@H:49]([CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH:58]=[CH2:59])[C:50](O)=[O:51])=[O:47])=[CH:42][N:41]=1.ON1C(=O)C2C(C3CC2C=C3)C1=O.Cl.CN(C)CCCN=C=NCC.CN(C)CCN>CN(C=O)C>[CH3:39][C:40]1[N:41]=[CH:42][C:43]([C:46]([NH:48][C@@H:49]([CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH:58]=[CH2:59])[C:50]([N:24]2[CH2:25][C@H:21]([O:20][C:11]3[C:10]([C:2]4[S:1][C:5]5[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=5[N:3]=4)=[N:19][C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]=3)[CH2:22][C@H:23]2[C:26]([NH:28][C@:29]2([C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH2:31][C@H:30]2[CH:32]=[CH2:33])=[O:27])=[O:51])=[O:47])=[CH:44][N:45]=1

参加物

7

反応物 5

HCID 66053N,N-DimethylethylenediamineHCID 895293a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dioneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67296764(s)-2-(2-Methylpyrimidine-5-carboxamido)non-8-enoic acidHCID 90815537(1R,2S)-ethyl 1-((2S,4R)-4-(3-(benzo[d]thiazol-2-yl)quinoxalin-2-yloxy)pyrrolidine-2-carboxamido)-2-vinylcyclopropanecarboxylate

生成物 1

HCID 90855515(1R,2S)-ethyl 1-((2S,4R)-1-((S)-2-(2-methylpyrimidine-5-carboxamido)non-8-enoyl)-4-(3-(benzo[d]thiazol-2-yl)quinoxalin-2-yloxy)pyrrolidine-2-carboxamido)-2-vinylcyclopropanecarboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

(1R,2S)-ethyl 1-((2S,4R)-4-(3-(benzo[d]thiazol-2-yl)quinoxalin-2-yloxy)pyrrolidine-2-carboxamido)-2-vinylcyclopropanecarboxylate, the title compound of Example 42a, N-hydroxy-5-norbornene-2,3-dicarboximide, and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride can be mixed and stirred in DMF for hours, followed by addition of N,N-dimethylethylene diamine. The reaction produces (1R,2S)-ethyl 1-((2S,4R)-1-((S)-2-(2-methylpyrimidine-5-carboxamido)non-8-enoyl)-4-(3-(benzo[d]thiazol-2-yl)quinoxalin-2-yloxy)pyrrolidine-2-carboxamido)-2-vinylcyclopropanecarboxylate, which can be dissolved in isopropyl acetate and extracted with aqueous H3PO4, and then extracted with aqueous K2HPO4. The product can be reacted with di-tert-butyldicarbonate in the presence of dimethylaminopyridine, followed by extraction with a mixture of a citric acid solution and a sodium chloride solution, to produce the title compound of Example 42b.

出典と根拠

ORDレコード
ord-28544b1e65b140c586fdd7a4997032fb
出典データセット
uspto-grants-2014_02
特許番号
US08642538B2

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