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Chloroacetyl chloride → HCID 178521458, 화합물

HRID 1047371
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HRID 1047371 반응식
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)=[O:4].FC(F)(F)C1C=CC(COC2C=CC(N3CCNCC3)=CC=2)=CC=1.ClCC(Cl)=O.[N+:58]([C:61]1[CH:66]=[CH:65][C:64]([NH:67][C@H:68]2[CH2:73][CH2:72][C@H:71]([OH:74])[CH2:70][CH2:69]2)=[CH:63][C:62]=1[C:75]([F:78])([F:77])[F:76])([O-:60])=[O:59]>>[N+:58]([C:61]1[CH:66]=[CH:65][C:64]([NH:67][C@H:68]2[CH2:73][CH2:72][C@H:71]([O:74][CH2:2][C:3]([N:5]3[CH2:10][CH2:9][N:8]([C:11]4[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]5[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=5)=[CH:13][CH:12]=4)[CH2:7][CH2:6]3)=[O:4])[CH2:70][CH2:69]2)=[CH:63][C:62]=1[C:75]([F:76])([F:77])[F:78])([O-:60])=[O:59]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 4

HCID 6577Chloroacetyl chlorideHCID 585767301-(4-(4-Trifluoromethyl-benzyloxy)-phenyl)-piperazineHCID 668519512-Chloro-1-{4-[4-(4-trifluoromethyl-benzyloxy)-phenyl]-piperazin-1-yl}-ethanoneHCID 178526690HCID 178526690, 화합물

생성물 1

HCID 178521458HCID 178521458, 화합물수율 46%

실험 절차

2-[Trans-4-(4-nitro-3-trifluoromethyl-phenylamino)-cyclohexyloxy]-1-{4-[4-(4-trifluoromethyl-benzyloxy)-phenyl]-piperazin-1-yl}-ethanone was prepared using a two-step synthesis. In the first step, 1-chloracetyl-4-[4-(4-trifluoromethyl-benzyloxy)-phenyl]-piperazine (also known as 2-chloro-1-{4-[4-(4-trifluoromethyl-benzyloxy)-phenyl]-piperazin-1-yl}-ethanone) was prepared with a 46% yield from 1-[4-(4-trifluoromethyl-benzyloxy)-phenyl]-piperazine (prepared in accordance with Example 19) and chloroacetyl chloride using the procedure illustrated in Example 4. In the second step, the 2-[trans-4-(4-nitro-3-trifluoromethyl-phenylamino)-cyclohexyloxy]-1-{4-[4-(4-trifluoromethyl-benzyloxy)-phenyl]-piperazin-1-yl}-ethanone was prepared from the 1-chloracetyl-4-[4-(4-trifluoromethyl-benzyloxy)-phenyl]-piperazine and trans-4-(4-nitro-3-trifluoromethyl-phenylamino)-cyclohexanol (prepared in accordance with Example 5) using the procedure illustrated in Example 11. This afforded the product as a yellow solid (10% yield). The structure was confirmed using Protocol II-A. Calculated mass=681; observed mass=681; HPLC retention time=4.75 min.

후처리

  1. customa two-step synthesis

출처 및 근거

ORD 기록
ord-e5299edb93824f53ae86ea072dd3b604
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08569495B2

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