Triethylamine → 4-Methyl-2-(2-(4-(3-(piperidin-1-yl)propoxy)phenyl)acetamido)thiophene-3-carboxamide

HRID 1519777노트

반응식

HRID 1519777 반응식
[N:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C:18]([OH:20])=O)=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[NH2:28][C:29]1[S:30][CH:31]=[C:32]([CH3:37])[C:33]=1[C:34]([NH2:36])=[O:35].CCN=C=NCCCN(C)C>CN(C=O)C.C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:37][C:32]1[C:33]([C:34]([NH2:36])=[O:35])=[C:29]([NH:28][C:18](=[O:20])[CH2:17][C:14]2[CH:13]=[CH:12][C:11]([O:10][CH2:9][CH2:8][CH2:7][N:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)=[CH:16][CH:15]=2)[S:30][CH:31]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 2938102-Amino-4-methylthiophene-3-carboxamideHCID 447696352-(4-(3-(Piperidin-1-yl)propoxy)phenyl)acetic acid

생성물 1

HCID 596366764-Methyl-2-(2-(4-(3-(piperidin-1-yl)propoxy)phenyl)acetamido)thiophene-3-carboxamide

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 22350042dichloromethane N,N-dimethylformamide용매

실험 절차

To a stirring mixture of 2-(4-(3-(piperidin-1-yl)propoxy)phenyl)acetic acid (800 mg) in DMF/DCM (6 mL, 1:1) was added triethylamine (1.2 mL), DMAP (180 mg), 2-amino-4-methylthiophene-3-carboxamide (440 mg), and EDCI (1.1 g). The reaction mixture was stirred at rt overnight, quenched with saturated NaHCO3 solution and extracted with EtOAc. The organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The crude product was purified via preparative HPLC to give 4-methyl-2-(2-(4-(3-(piperidin-1-yl)propoxy)phenyl)acetamido)thiophene-3-carboxamide. Method[7], MS(ESI) 416.2 [M+H], Retention time=2.254 min.

후처리

  1. customquenched with saturated NaHCO3 solution
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified via preparative HPLC

출처 및 근거

ORD 기록
ord-aabf344bb93042dea867c3bfc0cb1a78
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073891B2

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