Triethylamine → 4-(2-(5-bromo-2-fluorophenyl)pteridin-4-ylamino)-N-(3-(2-oxopyrrolidin-1-yl)propyl)nicotinamide

HRID 928267

반응식

HRID 928267 반응식
C([N:3](CC)CC)C.[Br:8][C:9]1[CH:10]=[CH:11][C:12]([F:35])=[C:13]([C:15]2[N:24]=[C:23]([NH:25][C:26]3[C:31]([C:32]([OH:34])=O)=[CH:30][N:29]=[CH:28][CH:27]=3)[C:22]3[C:17](=[N:18][CH:19]=[CH:20][N:21]=3)[N:16]=2)[CH:14]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.N[CH:70]([CH3:78])[CH2:71][N:72]1[CH2:76][CH2:75][CH2:74][C:73]1=[O:77]>C(Cl)Cl>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([F:35])=[C:13]([C:15]2[N:24]=[C:23]([NH:25][C:26]3[C:31]([C:32]([NH:3][CH2:78][CH2:70][CH2:71][N:72]4[CH2:76][CH2:75][CH2:74][C:73]4=[O:77])=[O:34])=[CH:30][N:29]=[CH:28][CH:27]=3)[C:22]3[C:17](=[N:18][CH:19]=[CH:20][N:21]=3)[N:16]=2)[CH:14]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 2724699PyBOPHCID 167870031-(2-Aminopropyl)-2-pyrrolidinoneHCID 577423744-[[2-(5-Bromo-2-fluorophenyl)pteridin-4-yl]amino]nicotinic Acid

생성물 1

HCID 119557904-(2-(5-bromo-2-fluorophenyl)pteridin-4-ylamino)-N-(3-(2-oxopyrrolidin-1-yl)propyl)nicotinamide수율 30.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Triethylamine (140 μL, 1.00 mmol) was slowly added to a solution of 4-[[2-(5-bromo-2-fluorophenyl)pteridin-4-yl]amino]nicotinic acid 16 (150 mg, 0.340 mmol), PyBOP (0.350 mg, 0.68 mmol), and 1-(β-aminopropyl)pyrrolidinone (97 mg, 0.68 mmol) in CH2Cl2 (10 mL). After 15 min at room temperature, the reaction mixture was evaporated and the residue purified by column chromatography (AcOEt/CH2Cl2, 2:1+1% triethylamine to AcOEt/CH2Cl2/MeOH, 7:2:1+1% triethylamine). The yellow powder was recrystallized from EtOH to give 58 mg of the title product 21 as yellow prisms (LCMS analysis).

후처리

  1. customthe reaction mixture was evaporated
  2. customthe residue purified by column chromatography (AcOEt/CH2Cl2, 2:1+1% triethylamine to AcOEt/CH2Cl2/MeOH, 7:2:1+1% triethylamine)
  3. customThe yellow powder was recrystallized from EtOH

출처 및 근거

ORD 기록
ord-702c0055a4154d8086e2321a7aa40a1f
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290502B2

연결된 노트

불러오는 중…