Diisopropylethylamine → Tris(1,1-dimethylethyl) 2-{2-chloro-5-fluoro-6-[3-methyl-3-(1-pyrrolidinyl)-1-azetidinyl]-4-pyrimidinyl}-1,1,2-hydrazinetricarboxylate

HRID 1366580Notes

Reaction equation

HRID 1366580 reaction equation
Cl.Cl.[CH3:3][C:4]1([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:7][NH:6][CH2:5]1.CCN(C(C)C)C(C)C.[CH3:22][C:23]([O:26][C:27]([N:29]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[N:30]([C:38]1[C:43]([F:44])=[C:42](Cl)[N:41]=[C:40]([Cl:46])[N:39]=1)[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[O:28])([CH3:25])[CH3:24]>CN(C=O)C>[CH3:25][C:23]([O:26][C:27]([N:29]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[N:30]([C:38]1[C:43]([F:44])=[C:42]([N:6]2[CH2:7][C:4]([CH3:3])([N:8]3[CH2:12][CH2:11][CH2:10][CH2:9]3)[CH2:5]2)[N:41]=[C:40]([Cl:46])[N:39]=1)[C:31]([O:33][C:34]([CH3:35])([CH3:36])[CH3:37])=[O:32])=[O:28])([CH3:22])[CH3:24]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 58000755Tris(1,1-dimethylethyl) 2-(2,6-dichloro-5-fluoro-4-pyrimidinyl)-1,1,2-hydrazinetricarboxylateHCID 669364881-(3-Methylazetidin-3-yl)pyrrolidine;dihydrochloride

Product 1

HCID 86636990Tris(1,1-dimethylethyl) 2-{2-chloro-5-fluoro-6-[3-methyl-3-(1-pyrrolidinyl)-1-azetidinyl]-4-pyrimidinyl}-1,1,2-hydrazinetricarboxylateYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1-(3-methyl-3-azetidinyl)pyrrolidine dihydrochloride (0.128 g, 86% pure, 0.52 mmol) in DMF (8 mL) at 0° C. was added DIPEA (0.34 mL, 1.94 mmol) followed immediately by tris(1,1-dimethylethyl)2-(2,6-dichloro-5-fluoro-4-pyrimidinyl)-1,1,2-hydrazinetricarboxylate (0.24, 0.49 mmol). The reaction was warmed up to rt and stirred overnight. The mixture was purified by RP-HPLC to provide tris(1,1-dimethylethyl)2-{2-chloro-5-fluoro-6-[3-methyl-3-(1-pyrrolidinyl)-1-azetidinyl]-4-pyrimidinyl}-1,1,2-hydrazinetricarboxylate (0.225 g, 77%). LCMS: (M+H)+: 601.2.

Workup

  1. customThe mixture was purified by RP-HPLC

Sources & evidence

ORD record
ord-342785dae79b42b6a329fbe7590b7193
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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