1-Chloro-N,N-2-trimethylpropenylamine → 4-{4-[(4-Cyano-1H-pyrrole-2-carbonyl)-amino]-3-cyclohex-1-enyl-phenyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1992039Notes

Reaction equation

HRID 1992039 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:8]([OH:10])=O)[NH:6][CH:7]=1)#[N:2].ClC(N(C)C)=C(C)C.[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([C:32]2[CH:37]=[CH:36][C:35]([NH2:38])=[C:34]([C:39]3[CH2:44][CH2:43][CH2:42][CH2:41][CH:40]=3)[CH:33]=2)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]>CC#N>[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([C:32]2[CH:37]=[CH:36][C:35]([NH:38][C:8]([C:5]3[NH:6][CH:7]=[C:3]([C:1]#[N:2])[CH:4]=3)=[O:10])=[C:34]([C:39]3[CH2:44][CH2:43][CH2:42][CH2:41][CH:40]=3)[CH:33]=2)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:20])[CH3:21]

Participants

5

Reactant 3

HCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 118048114-cyano-1H-pyrrole-2-carboxylic acidHCID 568348504-(4-Amino-3-cyclohex-1-enyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 586945824-{4-[(4-Cyano-1H-pyrrole-2-carbonyl)-amino]-3-cyclohex-1-enyl-phenyl]-piperidine-1-carboxylic acid tert-butyl esterYield 12.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A suspension of 101 mg (0.741 mmol) 4-cyano-1H-pyrrole-2-carboxylic acid (Canadian J. Chem. 59: 2673 (1981)) in 20 mL CH3CN was treated with 116 μL (0.741 mmol) (1-chloro-2-methyl-propenyl)-dimethylamine at RT for 20 min. The mixture was added to a solution of 220 mg (0.617 mmol) of 4-(4-amino-3-cyclohex-1-enyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (as prepared in the previous step) in 10 mL CH3CN, stirred at RT for 20 h and the solvents evaporated in vacuo. Silica gel chromatography of the residue on a Varian MegaBond Elut 25-gm column with 10-25% EtOAc-hexane afforded 36.0 mg (12%) of the title compound as an off-white solid: Mass spectrum (ESI, m/z): Calcd. for C24H27N4O3, 419.2 (M−C4H9+2H), found 419.1.

Workup

  1. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-e257f874fda9433997b3283e150c16d8
Source dataset
uspto-grants-2010_01
Patent number
US07645755B2

Reaction notes

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