tert-Butyl piperazine-1-carboxylate → HCID 10392905, compound

HRID 599145Notes

Reaction equation

HRID 599145 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[S:7][C:8]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=3)[N:13]=2)=[C:9]([CH3:11])[N:10]=1)=[O:4].[C:28]([O:32][C:33]([N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1)=[O:34])([CH3:31])([CH3:30])[CH3:29]>CN(C=O)C>[C:28]([O:32][C:33]([N:35]1[CH2:40][CH2:39][N:38]([CH2:2][C:3](=[O:4])[NH:5][C:6]2[S:7][C:8]([C:12]3[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=4)[N:13]=3)=[C:9]([CH3:11])[N:10]=2)[CH2:37][CH2:36]1)=[O:34])([CH3:31])([CH3:29])[CH3:30]

Participants

4

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 101793942-Chloro-N-{4-methyl-5-[2-(3-nitro-phenylamino)-pyrimidin-4-yl]-thiazol-2-yl}-acetamide

Product 1

HCID 10392905HCID 10392905, compoundYield 36.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-chloro-N-{4-methyl-5-[2-(3-nitro-phenylamino)-pyrimidin-4-yl]-thiazol-2-yl}-acetamide (40 mg, 0.1 mmol) in DMF (2 mL) was cooled on an ice bath. Piperazine-1-carboxylic acid tert-butyl ester (40 mg, 0.21 mmol) was added. After stirring at room temperature for 16 h, the reaction mixture was purified by preparative RP-HPLC (0-60% MeCN in 0.1% aq CF3COOH over 40 min, 9 mL/min) to afford the title compound (20 mg) as a light yellow solid. Anal. RP-HPLC: tR=16.9 min (0-60% MeCN in 0.1% aq CF3COOH over 20 min, 1 mL/min, purity >97%). 1H-NMR (CD3OD) δ: 2.65 (s, 3H, CH3), 2.87 (m, 4H, CH2), 3.36 (m, 4H, CH2), 4.66 (s, 2H, CH2), 7.71 (m, 1H, pyrimidinyl-H), 7.89 (t, 1H, J=8.1 Hz, Ph-H), 8.15 (m, 1H, Ph-H), 7.42 (m, 1H, Ph-H), 7.67 (m, 2H, pyrimidinyl-H & Ph-H).

Workup

  1. customthe reaction mixture was purified by preparative RP-HPLC (0-60% MeCN in 0.1% aq CF3COOH over 40 min, 9 mL/min)

Sources & evidence

ORD record
ord-f8288071a8bf4ec99ada17137c8c5983
Source dataset
uspto-grants-2011_03
Patent number
US07897605B2

Reaction notes

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