1-Methylpiperazine → tert-Butyl 2-(6-(4-methylpiperazin-1-yl)nicotinamido)-4-(thiophen-2-yl)phenylcarbamate

HRID 1907700Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of chloride 46 (0.15 g, 0.35 mmol) and N-methylpiperazine (0.5 mL, 4.5 mmol) was heated to 90° C. in a sealed tube for 18 h. The reaction mixture was then diluted with AcOEt, washed with saturated aqueous NaHCO3, brine, dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (eluent: 2:1 AcOEt:hexane) to afford title compound 48 (65 mg, 38% yield).

Workup

washwashed with saturated aqueous NaHCO3, brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by flash chromatography (eluent: 2:1 AcOEt:hexane)

Sources & evidence

ORD record: ord-d011d2244824419897e3efe46ef422eb
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598168B2

Reaction notes

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