1,1'-Carbonyldiimidazole → 4-[3-(5-Formyl-thiazol-2-yl)-1-(4-methyl-cyclohexyl)-ureido]-piperidine-1-carboxylic acid tert-butyl ester

HRID 2384223Notes

Reaction equation

HRID 2384223 reaction equation
[CH:1]([C:3]1[S:7][C:6]([NH2:8])=[N:5][CH:4]=1)=[O:2].[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19]([NH:22][CH:23]2[CH2:28][CH2:27][CH:26]([CH3:29])[CH2:25][CH2:24]2)[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C1N=CN([C:35](N2C=NC=C2)=[O:36])C=1>CN(C1C=CN=CC=1)C.C1COCC1>[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19]([N:22]([CH:23]2[CH2:28][CH2:27][CH:26]([CH3:29])[CH2:25][CH2:24]2)[C:35]([NH:8][C:6]2[S:7][C:3]([CH:1]=[O:2])=[CH:4][N:5]=2)=[O:36])[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 27377982-Amino-1,3-thiazole-5-carbaldehydeHCID 436521464-(4-Methyl-cyclohexylamino)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 578838034-[3-(5-Formyl-thiazol-2-yl)-1-(4-methyl-cyclohexyl)-ureido]-piperidine-1-carboxylic acid tert-butyl esterYield 357.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

Prepared in a manner similar to general procedure (C) using 5-formyl-2-aminothiazole (1.88 g, 14.6 mmol), 4-(4-methyl-cyclohexylamino)-piperidine-1-carboxylic acid tert-butyl ester (4.32 mg, 14.6 mmol), catalytic DMAP, CDI (2.60 g, 1.1 mmol) and THF with heating to 65° C. afforded 1.77 g (27%) of the desired product after purification.

Workup

  1. customPrepared in a manner similar to general procedure (C)

Sources & evidence

ORD record
ord-4a70e756a39e40e4aef03fd23a9ceede
Source dataset
uspto-grants-2012_09
Patent number
US08263634B2

Reaction notes

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