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

HRID 1411255노트

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HRID 1411255 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
45 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-986309b8482c457dabb3eccf3f790fae
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921576B2

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