Dimethylformamide → 2-(4-Ethoxycarboxypiperidino)carbonyl-4-(3,4-methylenedioxybenzyl)amino-6-chloroquinazoline hydrochloride

HRID 1003534노트

반응식

HRID 1003534 반응식
P(C#N)([O:6][CH2:7][CH3:8])(OCC)=O.C([N:13]([CH2:16][CH3:17])CC)C.[C:18]([C:21]1[N:30]=[C:29]([NH:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]3[O:39][CH2:40][O:41][C:35]=3[CH:34]=2)[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([Cl:42])[CH:27]=2)[N:22]=1)(O)=[O:19].N1CC[CH:46]([C:47]([O:49][CH2:50][CH3:51])=O)CC1.CN(C)C=[O:57]>O>[ClH:42].[CH2:47]([O:49][CH:50]1[CH2:17][CH2:16][N:13]([C:18]([C:21]2[N:30]=[C:29]([NH:31][CH2:32][C:33]3[CH:38]=[CH:37][C:36]4[O:39][CH2:40][O:41][C:35]=4[CH:34]=3)[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([Cl:42])[CH:27]=3)[N:22]=2)=[O:19])[CH:8]([C:7]([OH:6])=[O:57])[CH2:51]1)[CH3:46]

참가 물질

7

반응물 5

HCID 6228Dimethylformamide2회HCID 8471TriethylamineHCID 70770Ethyl 4-piperidinecarboxylateHCID 76257Diethyl cyanophosphonateHCID 187966952-Carboxy-4-(3,4-methylenedioxybenzyl)amino-6-chloroquinazoline

생성물 1

HCID 187967612-(4-Ethoxycarboxypiperidino)carbonyl-4-(3,4-methylenedioxybenzyl)amino-6-chloroquinazoline hydrochloride수율 82%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A solution of 0.50 ml (3.3 mmol) of diethyl cyanophosphate in 3 ml of dimethylformamide and 0.50 ml (3.6 mmol) of triethylamine were dropped, in this order, into a solution of 0.78 g (2.2 mmol) of 2-carboxy-4-(3,4-methylenedioxybenzyl)amino-6-chloroquinazoline and 0.50 g (3.2 mmol) of ethyl isonipecotate in 7 μl of dimethylformamide under cooling with ice and stirring. The obtained mixture was stirred under cooling with ice for 30 minutes and thereafter at room temperature for 3 hours, followed by the addition of water. The resulting mixture was extracted with ethyl acetate and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was distilled in a vacuum to remove the solvent. The residue was recrystallized from hydrochloric acid/ethanol/ether to give 0.96 g of the title compound.

후처리

  1. temperatureunder cooling with ice
  2. stirringThe obtained mixture was stirred
  3. temperatureunder cooling with ice for 30 minutes
  4. extractionThe resulting mixture was extracted with ethyl acetate
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. distillationThe filtrate was distilled in a vacuum
  8. customto remove the solvent
  9. customThe residue was recrystallized from hydrochloric acid/ethanol/ether

출처 및 근거

ORD 기록
ord-725062ef285b46bbb13fcbc7153c805c
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06046206

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