Chloroacetyl chloride → HCID 178510005, compound
Reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)=[O:4].N1(C2C=CC(C#N)=CC=2)CCNCC1.ClCC(Cl)=O.[N+:38]([C:41]1[CH:46]=[CH:45][C:44]([NH:47][C@H:48]2[CH2:53][CH2:52][C@H:51]([OH:54])[CH2:50][CH2:49]2)=[CH:43][C:42]=1[C:55]([F:58])([F:57])[F:56])([O-:40])=[O:39]>>[N+:38]([C:41]1[CH:46]=[CH:45][C:44]([NH:47][C@H:48]2[CH2:53][CH2:52][C@H:51]([O:54][CH2:2][C:3]([N:5]3[CH2:10][CH2:9][N:8]([C:11]4[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=4)[CH2:7][CH2:6]3)=[O:4])[CH2:50][CH2:49]2)=[CH:43][C:42]=1[C:55]([F:56])([F:57])[F:58])([O-:40])=[O:39]Participants
Procedure
4-(4-{2-[Trans-4-(4-nitro-3-trifluoromethyl-phenylamino)-cyclohexyloxy]-acetyl}-piperazin-1-yl)-benzonitrile was prepared using a two-step synthesis. In the first step, 1-chloracetyl-4-(4-benzonitrile)-piperazine (also known as 4-[4-(2-chloroacetyl)-piperazin-1-yl]-benzonitrile) was prepared from 4-(piperazin-1-yl)-benzonitrile and chloroacetyl chloride using the procedure illustrated in Example 4. In the second step, the 4-(4-{2-[trans-4-(4-nitro-3-trifluoromethyl-phenylamino)-cyclohexyloxy]-acetyl]-piperazin-1-yl)-benzonitrile was prepared from the 1-chloracetyl-4-(4-benzonitrile)-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 (39% yield). The structure was confirmed using Protocol II-A. Calculated mass=532; observed mass=532; HPLC retention time=4.14 min.
Workup
- custom4-(4-{2-[Trans-4-(4-nitro-3-trifluoromethyl-phenylamino)-cyclohexyloxy]-acetyl}-piperazin-1-yl)-benzonitrile was prepared
- customa two-step synthesis
Sources & evidence
- ORD record
- ord-72b5e4de0f84426d8e29b272d614aaad
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08569495B2
Reaction notes
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