Triethylamine → (5)-Tert-butyl 3-(4-(5-bromo-1h-pyrrolo [2,3-b]pyridin-4-yl)piperazin-1-yl)-2-(4-chlorophenyl)-3-oxopropyl(isopropyl)carbamate

HRID 79520노트

반응식

HRID 79520 반응식
N[C@H](CC1C=CC(Cl)=CC=1)[C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[C:16]([Br:17])=[CH:15][N:14]=[C:13]3[NH:18][CH:19]=[CH:20][C:12]=23)[CH2:7][CH2:6]1)=[O:4].[C:29]([O:33][C:34]([N:36]([CH:49]([CH3:51])[CH3:50])[CH2:37][C@H:38]([C:42]1[CH:47]=[CH:46][C:45]([Cl:48])=[CH:44][CH:43]=1)C(O)=O)=[O:35])([CH3:32])([CH3:31])[CH3:30].C1C=CC2N(O)N=NC=2C=1.O.CCN=C=NCCCN(C)C.C(N(CC)CC)C>C(Cl)Cl>[Br:17][C:16]1[C:11]([N:8]2[CH2:7][CH2:6][N:5]([C:3](=[O:4])[C@@H:38]([C:42]3[CH:43]=[CH:44][C:45]([Cl:48])=[CH:46][CH:47]=3)[CH2:37][N:36]([CH:49]([CH3:51])[CH3:50])[C:34](=[O:35])[O:33][C:29]([CH3:31])([CH3:32])[CH3:30])[CH2:10][CH2:9]2)=[C:12]2[CH:20]=[CH:19][NH:18][C:13]2=[N:14][CH:15]=1

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 44123672(R)-2-amino-1-(4-(5-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-3-(4-chlorophenyl)propan-1-oneHCID 59564929(2S)-3-[tert-butoxycarbonyl(isopropyl)amino]-2-(4-chlorophenyl)propanoic acid

생성물 1

HCID 68764847(5)-Tert-butyl 3-(4-(5-bromo-1h-pyrrolo [2,3-b]pyridin-4-yl)piperazin-1-yl)-2-(4-chlorophenyl)-3-oxopropyl(isopropyl)carbamate수율 60.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

5-Bromo-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine dihydrochloride (0.100 g, 0.282 mmol, see Example 1), (S)-3-(tert-butoxycarbonyl(isopropyl)amino)-2-(4-chlorophenyl)propanoic acid (0.145 g, 0.424 mmol, see Example H), HOBT-H2O (0.0606 g, 0.395 mmol), EDCI (0.0704 g, 0.367 mmol), and triethylamine (0.0394 mL, 0.282 mmol) were stirred in DCM (5 mL) at room temperature for 5 hours. The reaction was then quenched with saturated Na2CO3 and extracted into DCM. The organics were dried, filtered, and concentrated to give the crude product. Purification (500:6 DCM:MeOH) gave (S)-tert-butyl 3-(4-(5-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-2-(4-chlorophenyl)-3-oxopropyl(isopropyl)carbamate (0.103 g, 60.2% yield).

후처리

  1. customThe reaction was then quenched with saturated Na2CO3
  2. extractionextracted into DCM
  3. customThe organics were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the crude product
  7. customPurification (500:6 DCM:MeOH)

출처 및 근거

ORD 기록
ord-8a256ade946d4432a0c2d8bea1e9b971
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841304B2

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