1,2-Dichloroethane → 4-{N'-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-benzoyl]-hydrazinocarbonyl}-piperidine-1-carboxylic acid tert-butyl ester

HRID 403515노트

반응식

HRID 403515 반응식
[CH2:1]([C:3]1[C:13]([CH2:14][C:15]2[CH:23]=[CH:22][C:18]([C:19](O)=[O:20])=[CH:17][CH:16]=2)=[C:6]2[N:7]=[C:8]([CH3:12])[CH:9]=[C:10]([CH3:11])[N:5]2[N:4]=1)[CH3:2].CC1C=C(C)C=C(C)N=1.[C:33]([O:37][C:38]([N:40]1[CH2:45][CH2:44][CH:43]([C:46]([NH:48][NH2:49])=[O:47])[CH2:42][CH2:41]1)=[O:39])([CH3:36])([CH3:35])[CH3:34].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>C(OC(C)=O)(C)C.CCCCCCC.O.CN(C=O)C>[C:33]([O:37][C:38]([N:40]1[CH2:45][CH2:44][CH:43]([C:46]([NH:48][NH:49][C:19](=[O:20])[C:18]2[CH:17]=[CH:16][C:15]([CH2:14][C:13]3[C:3]([CH2:1][CH3:2])=[N:4][N:5]4[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[N:7][C:6]=34)=[CH:23][CH:22]=2)=[O:47])[CH2:42][CH2:41]1)=[O:39])([CH3:36])([CH3:34])[CH3:35]

참가 물질

9

반응물 5

HCID 111,2-DichloroethaneHCID 79532,4,6-TrimethylpyridineHCID 757711-HydroxybenzotriazoleHCID 22713165tert-Butyl 4-(hydrazinecarbonyl)piperidine-1-carboxylateHCID 683790634-((2-Ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)methyl)benzoic acid

생성물 1

HCID 683791124-{N'-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-benzoyl]-hydrazinocarbonyl}-piperidine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 18406121n-Heptane isopropyl acetate용매

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온도
23 °C

실험 절차

A 500 ml four-necked flask equipped with an overhead stirrer and a thermocouple was charged with acid 27 (10.0 g, 32.3 mmol, 1.0 eq), 120 ml of DMF and 2,4,6 trimethylpyridine (11.75 g, 96.9 mmol) under nitrogen purge. After stirring the reaction mixture for 30 min at 23° C., 4-hydrazinocarbonyl-piperidine-1-carboxylic acid tert-butyl ester (9.4 g, 38.7 mmol, 1.2 eq), EDC (12.3 g, 64.3 mmol), HOBT (1.48 g, 9.6 mmol) were added. The reaction mixture was stirred for 12 h at 23° C. After completion of the reaction, it was diluted with i-PrOAc/heptane (100 mL, 1:1) and followed by water (250 ml) at 23° C. The suspension was stirred for 1 h at 23° C. The solid was collected by filtration and washed with 50 ml of water. The wet product was dried at 40° C. for 12 h to obtain a white solid.

후처리

  1. customA 500 ml four-necked flask equipped with an overhead stirrer
  2. custompurge
  3. stirringThe reaction mixture was stirred for 12 h at 23° C
  4. customAfter completion of the reaction, it
  5. stirringThe suspension was stirred for 1 h at 23° C
  6. filtrationThe solid was collected by filtration
  7. washwashed with 50 ml of water
  8. customThe wet product was dried at 40° C. for 12 h
  9. customto obtain a white solid

출처 및 근거

ORD 기록
ord-e1163b34b1ed47309ae8190581658bbe
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748435B2

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