4-Methylmorpholine → HCID 10114657, 화합물

HRID 612021노트

반응식

HRID 612021 반응식
ClC(OCC(C)C)=O.CN1CCOCC1.[CH3:16][N:17]([CH3:24])[CH2:18][C:19]#[C:20][C:21](O)=[O:22].[NH2:25][C:26]1[CH:27]=[C:28]2[C:33](=[CH:34][CH:35]=1)[N:32]=[CH:31][C:30]([C:36]#[N:37])=[C:29]2[NH:38][C:39]1[CH:44]=[CH:43][CH:42]=[C:41]([Br:45])[CH:40]=1>O1CCCC1.N1C=CC=CC=1>[Br:45][C:41]1[CH:40]=[C:39]([NH:38][C:29]2[C:28]3[C:33](=[CH:34][CH:35]=[C:26]([NH:25][C:21](=[O:22])[C:20]#[C:19][CH2:18][N:17]([CH3:24])[CH3:16])[CH:27]=3)[N:32]=[CH:31][C:30]=2[C:36]#[N:37])[CH:44]=[CH:43][CH:42]=1

참가 물질

7

반응물 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 99677126-Amino-4-(3-bromophenylamino)quinoline-3-carbonitrileHCID 150797524-(Dimethylamino)but-2-ynoic acid

생성물 1

HCID 10114657HCID 10114657, 화합물수율 21.8%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 8028Tetrahydrofuran용매

실험 절차

Isobutyl chloroformate(0.260 g, 1.91 mmol) and N-methylmorpholine(0.594 g, 5.88 mmol) were added to an ice cold solution of 0.370 g (2.94 mmol) of 4-dimethylamino-2-butynoic acid in 50 mL of tetrahydrofuran under N2. After stirring for 30 min, a solution of 0.500 g (01.47 mmol) of 6-amino-4-[(3-bromophenyl)amino]-3-quinolinecarbonitrile in 10 mL of pyridine was added and the mixture was stirred at 0° C. for 2 h. The reaction was quenched with ice water, and then poured into saturated sodium bicarbonate and brine. The product was collected, washed with ethyl acetate, and dried in vacuo to give 0.144 g (21%) of yellow solid; ESMS m/z 448.0 (M+H+); mp 114-118° C.

후처리

  1. stirringthe mixture was stirred at 0° C. for 2 h
  2. customThe reaction was quenched with ice water
  3. additionpoured into saturated sodium bicarbonate and brine
  4. customThe product was collected
  5. washwashed with ethyl acetate
  6. customdried in vacuo

출처 및 근거

ORD 기록
ord-701f158aef0f4ab0afe8376c63c841d9
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06002008

반응 노트

불러오는 중…