4-Methylmorpholine → HCID 15550658, 화합물

HRID 276832노트

반응식

HRID 276832 반응식
[C:1]([OH:6])(=O)[C:2]#[C:3][CH3:4].CN1CCOCC1.ClC(OCC(C)C)=O.[NH2:22][C:23]1[CH:24]=[C:25]2[C:30](=[N:31][CH:32]=1)[N:29]=[CH:28][C:27]([C:33]#[N:34])=[C:26]2[NH:35][C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([Br:42])[CH:37]=1>O1CCCC1.N1C=CC=CC=1>[Br:42][C:38]1[CH:37]=[C:36]([NH:35][C:26]2[C:27]([C:33]#[N:34])=[CH:28][N:29]=[C:30]3[C:25]=2[CH:24]=[C:23]([NH:22][C:1](=[O:6])[C:2]#[C:3][CH3:4])[CH:32]=[N:31]3)[CH:41]=[CH:40][CH:39]=1

참가 물질

7

반응물 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 685352-Butynoic acidHCID 99498136-Amino-4-(3-bromo-phenylamino)-[1,8]naphthyridine-3-carbonitrile

생성물 1

HCID 15550658HCID 15550658, 화합물수율 29.8%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 0.85 g (10.1 mmol) of tetrolic acid and 1.8 g (17.96 mmol) of N-methyl morpholine in 18 ml of tetrahydrofuran was stirred at 0° C. as 1.35 g (9.9 mmol) of isobutyl chloroformate was slowly added. After 15 min, this mixture was added to a solution of 1.3 g (3.8 mmol) of 6-amino-4-(3-bromo-phenylamino)-[1.8]naphthyridine-3-carbonitrile and 5 mg of 4-N,N-dimethylamino-pyridine in 10 ml pyridine. The mixture was stirred a room temperature for 2.25 hr. The tetrahydrofuran was removed, diluted sodium bicarbonate was added, and the solid was collected via filtration. The solid was air dried and chromatographed on silica gel eluting with ethyl acetate-methanol mixtures giving 0.46 g of the title compound as a tan powder: mass spectrum (electrospray, m/e): M+H 408.1, 406.0.

후처리

  1. additionwas slowly added
  2. customThe tetrahydrofuran was removed
  3. additiondiluted sodium bicarbonate was added
  4. filtrationthe solid was collected via filtration
  5. customdried
  6. customchromatographed on silica gel eluting with ethyl acetate-methanol

출처 및 근거

ORD 기록
ord-7ef15ce723c44f52b36cff52956d54c5
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06355636B1

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