1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (R)-tert-butyl 3-(4-chlorophenyl)-1-(4-(5-(3-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-1-oxopropan-2-ylcarbamate

HRID 79534노트

반응식

HRID 79534 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:10]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[C:11]3[CH:17]=[CH:16][NH:15][C:12]3=[N:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1.[C:24]([O:28][C:29]([NH:31][C@H:32]([CH2:36][C:37]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=1)[C:33](O)=[O:34])=[O:30])([CH3:27])([CH3:26])[CH3:25].C1C=CC2N(O)N=NC=2C=1.O.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:43][C:40]1[CH:41]=[CH:42][C:37]([CH2:36][C@@H:32]([NH:31][C:29](=[O:30])[O:28][C:24]([CH3:26])([CH3:25])[CH3:27])[C:33]([N:21]2[CH2:22][CH2:23][N:18]([C:10]3[C:9]([C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=4)=[CH:14][N:13]=[C:12]4[NH:15][CH:16]=[CH:17][C:11]=34)[CH2:19][CH2:20]2)=[O:34])=[CH:38][CH:39]=1

참가 물질

7

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 7018791N-Boc-4-chloro-D-phenylalanineHCID 687616565-(3-Methoxyphenyl)-4-(piperazin-1-yl)-1h-pyrrolo[2,3-b]pyridine

생성물 1

HCID 68761315(R)-tert-butyl 3-(4-chlorophenyl)-1-(4-(5-(3-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-1-oxopropan-2-ylcarbamate수율 54.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

5-(3-Methoxyphenyl)-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyri dine (0.045 g, 0.118 mmol) and (R)-2-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propanoic acid (0.0425 g, 0.142 mmol) were placed in DCM (3 mL). HOBT-H2O (0.0253 g, 0.165 mmol), EDCI (0.0294 g, 0.153 mmol), and DIEA (d 0.742; 0.103 mL, 0.591 mmol) were then added, and the reaction was stirred for 2 hours. The reaction was then quenched with saturated Na2CO3 and extracted with DCM. The product was dried, filtered, and concentrated to give the crude product. The crude product was purified (500:5 DCM:MeOH) to yield (R)-tert-butyl 3-(4-chlorophenyl)-1-(4-(5-(3-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-1-oxopropan-2-ylcarbamate (0.038 g, 54.6% yield).

후처리

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

출처 및 근거

ORD 기록
ord-3f45966adba1418e85c9174311e846e8
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841304B2

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