Sodium hydride → Tert-butyl (trans)-2-(1,1'-biphenyl-4-yl)cyclopropyl(2-(4-methylpiperazin-1-yl)-2-oxoethyl)carbamate

HRID 38117

반응식

HRID 38117 반응식
[H-].[Na+].[C:3]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:8]=[CH:7][C:6]([C@@H:9]2[CH2:11][C@H:10]2[NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:5][CH:4]=1.Cl[CH2:27][C:28]([N:30]1[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]1)=[O:29]>CN(C=O)C>[C:3]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:8]=[CH:7][C:6]([C@@H:9]2[CH2:11][C@H:10]2[N:12]([CH2:27][C:28]([N:30]2[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]2)=[O:29])[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:5][CH:4]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 8181732-Chloro-1-(4-methylpiperazin-1-yl)ethanoneHCID 86658778Tert-butyl(trans)-2-(1,1'-biphenyl-4-yl)cyclopropylcarbamate

생성물 1

HCID 67448639Tert-butyl (trans)-2-(1,1'-biphenyl-4-yl)cyclopropyl(2-(4-methylpiperazin-1-yl)-2-oxoethyl)carbamate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

To a suspension of 1.5 equiv of NaH in dry DMF (10 vols) at 0° C. was added a solution of tert-butyl(trans)-2-(1,1′-biphenyl-4-yl)cyclopropylcarbamate derivative (1 equiv) in dry DMF (2 vols) and stirr for 30 mins. Then, added a solution of 1-(chloroacetyl)-4-methylpiperazine (1.5 equiv) in dry DMF (10 mL) at 0° C., stirred for 1 h at 0° C. to RT. The progress of the reaction was monitored by TLC. After completion, reaction mixture was poured into ice water and extracted with EtOAC. The combined extracts were washed with water, brine, dried over anhydrous Na2SO4, filtered and evaporated. The crude residue was purifying by preparative HPLC to get tert-butyl (trans)-2-(1,1′-biphenyl-4-yl)cyclopropyl(2-(4-methylpiperazin-1-yl)-2-oxoethyl)carbamate derivative

후처리

  1. customAfter completion, reaction mixture
  2. extractionextracted with EtOAC
  3. washThe combined extracts were washed with water, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude residue was purifying by preparative HPLC

출처 및 근거

ORD 기록
ord-c32a277b93bd4a4fa6a6d77eca32ddec
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524717B2

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