Trifluoroacetic acid → {4-[1-Benzyl-6-(2-piperidin-4-yl-(E)-vinyl)-1H-indazol-3-yl]-piperidin-1-yl}-acetic acid trifluoroacetate
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:32]4[CH2:37][CH2:36][N:35]([CH2:38][C:39]([O:41]C(C)(C)C)=[O:40])[CH2:34][CH2:33]4)=[N:21][N:22]3[CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[F:46][C:47]([F:52])([F:51])[C:48]([OH:50])=[O:49]>>[F:46][C:47]([F:52])([F:51])[C:48]([OH:50])=[O:49].[CH2:25]([N:22]1[C:23]2[C:19](=[CH:18][CH:17]=[C:16](/[CH:15]=[CH:14]/[CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[CH:24]=2)[C:20]([CH:32]2[CH2:37][CH2:36][N:35]([CH2:38][C:39]([OH:41])=[O:40])[CH2:34][CH2:33]2)=[N:21]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1Participants
3
Reactant 2
Product 1
Procedure
4-{2-[1-Benzyl-3-(1-tert-butoxycarbonylmethyl-piperidin-4-yl]-1H-indazol-6-yl]-(E)-vinyl}-piperidine-1carboxylic acid tert-butyl ester (95 mg, 0.154 mmol) was treated with trifluoroacetic acid (2 ml) and the mixture stirred under nitrogen for 18 h. The solution was concentrated in vacuo and the residue dried in vacuo for 1 h. The resulting yellow gum was saturated with dry diethyl ether (5 ml); the supernatant was decanted off and the solid was washed with ether (5 ml) and dried in vacuo at 60° for 18 h to give the title compound (94 mg) as a pale yellow solid (94 mg).
Workup
- concentrationThe solution was concentrated in vacuo
- customthe residue dried in vacuo for 1 h
- customthe supernatant was decanted off
- washthe solid was washed with ether (5 ml)
- customdried in vacuo at 60° for 18 h
Sources & evidence
- ORD record
- ord-dffcb20f5cc04208b48d4769647532f9
- Source dataset
- uspto-grants-1999_01
- Patent number
- US05861414
Reaction notes
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