2-Dimethylaminopyridine → Methyl 5-chloro-1-((4-((dimethylamino)methyl)thiazol-2-yl)carbamoyl)spiro[indoline-3,3'-pyrrolidine]-1'-carboxylate

HRID 1411255ノート

反応式

HRID 1411255 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12]([C:15]([O:17][CH3:18])=[O:16])[CH2:11]3)[CH2:9][NH:8][C:5]2=[CH:6][CH:7]=1.[CH3:19][N:20]([CH2:22][C:23]1[N:24]=[C:25]([NH2:28])[S:26][CH:27]=1)[CH3:21].[C:29](N1C=CN=C1)(N1C=CN=C1)=[O:30].CN(C1C=CC=CN=1)C>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12]([C:15]([O:17][CH3:18])=[O:16])[CH2:11]3)[CH2:9][N:8]([C:29](=[O:30])[NH:28][C:25]3[S:26][CH:27]=[C:23]([CH2:22][N:20]([CH3:21])[CH3:19])[N:24]=3)[C:5]2=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 218852-DimethylaminopyridineHCID 682631,1'-CarbonyldiimidazoleHCID 3516854-[(Dimethylamino)methyl]-1,3-thiazol-2-amineHCID 89520496Methyl 5-chlorospiro[indoline-3,3'-pyrrolidine]-1'-carboxylate

生成物 1

HCID 90449933Methyl 5-chloro-1-((4-((dimethylamino)methyl)thiazol-2-yl)carbamoyl)spiro[indoline-3,3'-pyrrolidine]-1'-carboxylate収率 35.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
45 °C

実験手順

The methyl 5-chlorospiro[indoline-3,3′-pyrrolidine]-1′-carboxylate (20 mg, 0.076 mmol) obtained in Step 1 of Example 89 was dissolved in tetrahydrofuran (1.0 mL). Thereafter, the 4-((dimethylamino)methyl)thiazole-2-amine (12 mg, 0.076 mmol) synthesized by a method described in the known methods (International Publication WO2008/086047 etc.) or a method similar thereto, carbonyldiimidazole (24 mg, 0.152 mmol), and dimethylaminopyridine (1.0 mg, 0.008 mmol) were added to the above obtained solution, and the thus obtained mixture was then stirred at 45° C. for 12 hours. Thereafter, the reaction solution was concentrated in vacuo, and the obtained residue was then purified by silica gel column chromatography (chloroform:methanol=10:1) to obtain the captioned compound (12 mg, 34%) in the form of a white solid.

後処理

  1. concentrationThereafter, the reaction solution was concentrated in vacuo
  2. customthe obtained residue was then purified by silica gel column chromatography (chloroform:methanol=10:1)

出典と根拠

ORDレコード
ord-986309b8482c457dabb3eccf3f790fae
出典データセット
uspto-grants-2014_12
特許番号
US08921576B2

反応ノート

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