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

HRID 928267

反応式

HRID 928267 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-702c0055a4154d8086e2321a7aa40a1f
出典データセット
uspto-grants-2016_03
特許番号
US09290502B2

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