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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-butyl 3-(2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamido)-3-methylpyrrolidine-1-carboxylate

HRID 246622
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HRID 246622 반응식
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]3[N:13]=[C:14]4[C:20]([C:21](O)=[O:22])=[CH:19][NH:18][C:15]4=[N:16][CH:17]=3)=[N:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.[NH2:35][C:36]1([CH3:48])[CH2:40][CH2:39][N:38]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:37]1>CN(C=O)C.CN(C1C=CN=CC=1)C>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]3[N:13]=[C:14]4[C:20]([C:21]([NH:35][C:36]5([CH3:48])[CH2:40][CH2:39][N:38]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:37]5)=[O:22])=[CH:19][NH:18][C:15]4=[N:16][CH:17]=3)=[N:7][N:8]2[CH3:11])=[CH:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 57415917tert-Butyl 3-amino-3-methylpyrrolidine-1-carboxylateHCID 712796392-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

생성물 1

HCID 71280536tert-butyl 3-(2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamido)-3-methylpyrrolidine-1-carboxylate수율 65.2%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매
HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (100 mg, 0.32 mmol) in 6 mL of DMF were added EDCI (123 mmol, 0.64 mmol), DMAP (110 mg, 0.90 mmol) and tert-butyl 3-amino-3-methylpyrrolidine-1-carboxylate (128 mg, 0.64 mmol) in one portion at room temperature and the mixture stirred for 16 hours. The solvent was evaporated at 70° C. under reduced pressure, the residue was triturated with petroleum ether then decanted and dried to give crude tert-butyl 3-(2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamido)-3-methylpyrrolidine-1-carboxylate (103 mg, 65.2%) as a yellow solid which was used for the next step without further purification.

후처리

  1. customThe solvent was evaporated at 70° C. under reduced pressure
  2. customthe residue was triturated with petroleum ether
  3. customthen decanted
  4. customdried

출처 및 근거

ORD 기록
ord-8939d25b15c24236a5ade9f4a40a9a98
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08658646B2

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