tert-butyl N-(1-carbamothioylpiperidin-4-yl)carbamate → Ethyl 2-(4-aminopiperidin-1-yl)-4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-1,3-thiazole-5-carboxylate hydrochloride

HRID 2233868Notes

Reaction equation

HRID 2233868 reaction equation
[NH2:1][C:2]([N:4]1[CH2:9][CH2:8][CH:7]([NH:10]C(=O)OC(C)(C)C)[CH2:6][CH2:5]1)=[S:3].[Cl:18][CH:19]([C:25](=O)[CH2:26][N:27]1[C:35](=[O:36])[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]1=[O:37])[C:20]([O:22][CH2:23][CH3:24])=[O:21]>>[ClH:18].[NH2:10][CH:7]1[CH2:6][CH2:5][N:4]([C:2]2[S:3][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:25]([CH2:26][N:27]3[C:35](=[O:36])[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[C:28]3=[O:37])[N:1]=2)[CH2:9][CH2:8]1

Participants

3

Reactant 2

HCID 59296117tert-butyl N-(1-carbamothioylpiperidin-4-yl)carbamate2×HCID 86608257ethyl 2-chloro-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-oxobutanoate2×

Product 1

HCID 68579924Ethyl 2-(4-aminopiperidin-1-yl)-4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-1,3-thiazole-5-carboxylate hydrochloride

Procedure

The title compound was prepared in a manner analogous to Intermediate 126 starting from tert-butyl [1-(aminocarbonothioyl)piperidin-4-yl]carbamate (Intermediate 125) and ethyl 2-chloro-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-oxobutanoate (Intermediate 35).

Sources & evidence

ORD record
ord-1bb41547ebe549769fc4029f17c45a98
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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