Trifluoroacetic acid → (4-{1-(4-Chloro-benzyl)-6-[2-piperidin-4-yl-(E)-vinyl]-1H-indazol-3-yl}-piperidin-1-yl)-acetic acid trifluoroacetate

HRID 343412Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][CH:11](/[CH:14]=[CH:15]/[C:16]2[CH:24]=[C:23]3[C:19]([C:20]([CH:33]4[CH2:38][CH2:37][N:36]([CH2:39][C:40]([O:42]C(C)(C)C)=[O:41])[CH2:35][CH2:34]4)=[N:21][N:22]3[CH2:25][C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[F:47][C:48]([F:53])([F:52])[C:49]([OH:51])=[O:50]>>[F:47][C:48]([F:53])([F:52])[C:49]([OH:51])=[O:50].[Cl:32][C:29]1[CH:28]=[CH:27][C:26]([CH2:25][N:22]2[C:23]3[C:19](=[CH:18][CH:17]=[C:16](/[CH:15]=[CH:14]/[CH:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)[CH:24]=3)[C:20]([CH:33]3[CH2:38][CH2:37][N:36]([CH2:39][C:40]([OH:42])=[O:41])[CH2:35][CH2:34]3)=[N:21]2)=[CH:31][CH:30]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 700971444-{2-[3-(1-tert-Butoxycarbonylmethyl-piperidin-4-yl)-1-(4-chloro-benzyl)-1H-indazol-6-yl]-(E)-vinyl}-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 67593246(4-{1-(4-Chloro-benzyl)-6-[2-piperidin-4-yl-(E)-vinyl]-1H-indazol-3-yl}-piperidin-1-yl)-acetic acid trifluoroacetateYield 86%

Procedure

A solution of 4-{2-[3-(1-tert-butoxycarbonylmethyl-piperidin-4-yl)-1-(4-chloro-benzyl)-1H-indazol-6-yl]-(E)-vinyl}-piperidine-1-carboxylic acid tert-butyl ester (0.152 g, 0.234 mmol) in trifluoroacetic acid (4 ml) was stirred at 23° for 3 h. The solvent was removed in vacuo and the residue was triturated with ether to give the title compound as an ivory solid (0.148 g, 86%).

Workup

customThe solvent was removed in vacuo
customthe residue was triturated with ether

Sources & evidence

ORD record: ord-460f856100694515a62f32f07c69e234
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05861414

Reaction notes

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