Potassium Carbonate → 4-(3-Cyanomethoxy-5-methoxy-benzoylamino)-piperidine-1-carboxylic acid tert-butyl ester
Reaction equation
[C:1]([CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:17]=[C:18]([O:20][CH3:21])[CH:19]=1)[C:8]([NH:10][CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)=[O:9])#[N:2].[C:22]([O:26][C:27](N1CCC(NC(=O)C2C=C(OC)C=C(O)C=2)CC1)=[O:28])([CH3:25])([CH3:24])[CH3:23].BrCC#N.C(=O)([O-])[O-].[K+].[K+]>CC#N>[C:22]([O:26][C:27]([N:14]1[CH2:13][CH2:12][CH:11]([NH:10][C:8](=[O:9])[C:7]2[CH:17]=[C:18]([O:20][CH3:21])[CH:19]=[C:5]([O:4][CH2:3][C:1]#[N:2])[CH:6]=2)[CH2:16][CH2:15]1)=[O:28])([CH3:25])([CH3:24])[CH3:23]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
In analogy to the procedure described in example 50k), 3-cyanomethoxy-5-methoxy-N-piperidin-4-yl-benzamide [prepared by i) reaction of 4-(3-hydroxy-5-methoxy-benzoylamino)-piperidine-1-carboxylic acid tert-butyl ester (example 168a) with bromo-acetonitrile in MeCN at rt in the presence of anhydrous potassium carbonate to give 4-(3-cyanomethoxy-5-methoxy-benzoylamino)-piperidine-1-carboxylic acid tert-butyl ester; ii) Boc cleavage using trifluoro acetic acid (90%) in MeCl2 at rt in analogy to the procedure described in example 50i)] was reacted with 3,5-diethoxy-4-fluoro-benzaldehyde (example 50 g), sodium cyanoborohydride, N-ethyl-diisopropylamine and acetic acid in ethanol at 50° C. to yield the title compound as off-white solid. MS: 486.3 (MH+).
Workup
- customprepared by i)
Sources & evidence
- ORD record
- ord-08b5a3ac03a54c37b408747142b25d9a
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07772253B2
Reaction notes
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