Acetic Anhydride → 6-chloro-2-methyl-3-{4-[3-(1-piperidinyl)propoxy]phenyl}pyrido[3,4-d]pyrimidin-4(3H)-one

HRID 2386933노트

반응식

HRID 2386933 반응식
NC1C(C(O)=O)=CC(Cl)=NC=1.C(OC(=O)C)(=O)C.[Cl:19][C:20]1[N:38]=[CH:37][C:23]2[N:24]=[C:25]([CH3:36])[N:26]([C:29]3[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=3)[C:27](=[O:28])[C:22]=2[CH:21]=1.Br.Br[CH2:41][CH2:42][CH2:43][N:44]1[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:19][C:20]1[N:38]=[CH:37][C:23]2[N:24]=[C:25]([CH3:36])[N:26]([C:29]3[CH:30]=[CH:31][C:32]([O:35][CH2:41][CH2:42][CH2:43][N:44]4[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]4)=[CH:33][CH:34]=3)[C:27](=[O:28])[C:22]=2[CH:21]=1

참가 물질

7

반응물 5

HCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 201357721-(3-Bromopropyl)piperidine HydrobromideHCID 227367915-Amino-2-chloro-isonicotinic acidHCID 231511466-chloro-2-methyl-3-(4-hydroxyphenyl)pyrido[3,4-d]pyrimidin-4(3H)-one

생성물 1

HCID 117185676-chloro-2-methyl-3-{4-[3-(1-piperidinyl)propoxy]phenyl}pyrido[3,4-d]pyrimidin-4(3H)-one수율 60%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

Using 5-amino-4-carboxy-2-chloropyridine and acetic anhydride as starting materials, 6-chloro-2-methyl-3-(4-hydroxyphenyl)pyrido[3,4-d]pyrimidin-4(3H)-one synthesized according to Example 1-(1) and -(2) (52 mg, 0.18 mmol), 1-(3-bromopropyl)piperidine hydrobromide (78 mg, 0.27 mmol) and potassium carbonate (100 mg, 0.72 mmol) were mixed in dimethylformamide (1 mL) and stirred at 80° C. for 1 hour. The solvent was distilled off under reduced pressure, distilled water was added, and the mixture was extracted with ethyl acetate. The organic phase was washed with distilled water, and dried with anhydrous sodium sulfate. The title compound (45 mg, 60%) was obtained as colorless crystals by purifying with silica gel column chromatography (chloroform/methanol=30/1) and recrystallizing (ethanol).

후처리

  1. customsynthesized
  2. distillationThe solvent was distilled off under reduced pressure
  3. distillationdistilled water
  4. additionwas added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic phase was washed with distilled water
  7. dry with materialdried with anhydrous sodium sulfate

출처 및 근거

ORD 기록
ord-6c02d917ca0340a4bb2e288b17e50d41
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268842B2

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