Trifluoroacetic acid → HCID 68283271, compound
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([C:13](=[O:24])[NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:17]=2[F:23])[N:9]1[C:25](=[O:39])[NH:26][C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]([C:36](=[O:38])[NH2:37])[CH:28]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:40](O)([C:42](F)(F)F)=[O:41].C(OC([N:54]1[CH2:58][CH2:57][C@H:56]([C:59](=[O:70])[NH:60][CH2:61][C:62]2[CH:67]=[CH:66][CH:65]=[C:64]([Cl:68])[C:63]=2[F:69])[NH:55]1)=O)(C)(C)C>>[Cl:68][C:64]1[C:63]([F:69])=[C:62]([CH:67]=[CH:66][CH:65]=1)[CH2:61][NH:60][C:59]([C@@H:56]1[N:55]([C:40](=[O:41])[CH2:42][C:27]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[N:29]([C:36]([NH2:37])=[O:38])[CH:28]=2)[NH:54][CH2:58][CH2:57]1)=[O:70].[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([C:13](=[O:24])[NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:17]=2[F:23])[N:9]1[C:25](=[O:39])[NH:26][C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]([C:36](=[O:38])[NH2:37])[CH:28]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
5
Procedure
The title compound was prepared from (R)-2-(1-carbamoyl-1H-indol-3-ylcarbamoyl)-3-(3-chloro-2-fluoro-benzylcarbamoyl)-pyrazolidine-1-carboxylic acid tert-butyl ester according to the procedure described for the preparation of Example 432 using 10 equivalents of TFA for the Boc deprotection. MS: 459 [M+H]+; tR (HPLC conditions b): 3.73 min. (R)-2-(1-Carbamoyl-1H-indol-3-ylcarbamoyl)-3-(3-chloro-2-fluoro-benzylcarbamoyl)-pyrazolidine-1-carboxylic acid tert-butyl ester was prepared as described in Scheme D5 step C using (R)-3-(3-chloro-2-fluoro-benzylcarbamoyl)-pyrazolidine-1-carboxylic acid tert-butyl ester (prepared as described in Scheme B5).
Sources & evidence
- ORD record
- ord-8ca65d03406d4fe19e8ba9eb7ff92f61
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09085555B2
Reaction notes
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