Triethylamine → 1-((8-(2-Ethyl-6-methylbenzylamino)-2,3-dimethylimidazo[1,2-a]pyridin-6-yl)carbonyl)-2-(s)-pyrrolidinecarboxamide

HRID 427476

반응식

HRID 427476 반응식
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([NH:10][CH2:11][C:12]3[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:19][CH3:20])=[CH:8][C:7]([C:21](O)=[O:22])=[CH:6][N:5]2[C:24]=1[CH3:25].[B-](F)(F)(F)F.CN(C(ON1N=NC2C1=CC=CC=2)=[N+](C)C)C.C(N(CC)CC)C.[NH:55]1[CH2:62][CH2:61][CH2:60][C@H:56]1[C:57]([NH2:59])=[O:58]>C(Cl)Cl>[CH2:19]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([CH3:18])[C:12]=1[CH2:11][NH:10][C:9]1[C:4]2[N:5]([C:24]([CH3:25])=[C:2]([CH3:1])[N:3]=2)[CH:6]=[C:7]([C:21]([N:55]2[CH2:62][CH2:61][CH2:60][C@H:56]2[C:57]([NH2:59])=[O:58])=[O:22])[CH:8]=1)[CH3:20]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 111306L-ProlinamideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 118239362,3-Dimethyl-8-(2-ethyl-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxylic acid

생성물 1

HCID 98242001-((8-(2-Ethyl-6-methylbenzylamino)-2,3-dimethylimidazo[1,2-a]pyridin-6-yl)carbonyl)-2-(s)-pyrrolidinecarboxamide수율 36.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

2,3-dimethyl-8-(2-ethyl-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxylic acid (0.15 g, 0.44 mmol), o-Benzotriazol-1-yl-N,N,N′,N′-Tetramethyluronium tetrafluoroborate (TBTU)(0.14 g, 0.45 mmol) and triethylamine (0.05 g, 0.5 mmol) were added to methylene chloride (10 ml) and the mixture was stirred for 10 min. (S)-prolinamide (0.016 g, 0.45 mmol) was added and the reaction mixture was stirred at ambient temperature for 1 h. The solvent was evaporated under reduced pressure and purification of the residue by column chromatography on silica gel using methylene chloride:methanol (9:1) as eluent and crystallization from diethyl ether gave 0.07 g (36%) of the title compound.

후처리

  1. additionwas added
  2. customThe solvent was evaporated under reduced pressure and purification of the residue by column chromatography on silica gel
  3. customcrystallization from diethyl ether

출처 및 근거

ORD 기록
ord-0e78413df04e46e3ad2bd563c26aa502
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313136B1

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