Reaction equation
[CH2:1](Cl)[CH2:2]Cl.[CH:5]([N:8](C(C)C)CC)(C)[CH3:6].C(N)C1C=CC=CC=1.C(OC(N1CCCC1[C:34](=O)[NH:35][C:36]1[CH:41]=C(Cl)[CH:39]=[CH:38][C:37]=1[C:43](=[O:52])[NH:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=O)(C)(C)C.Cl[CH2:55][Cl:56]>>[CH2:45]([N:44]1[C:43](=[O:52])[C:37]2[C:36](=[CH:41][C:55]([Cl:56])=[CH:39][CH:38]=2)[N:35]([CH:2]2[CH2:1][CH2:6][CH2:5][NH:8]2)[CH2:34]1)[C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1Participants
Reactant 5
Product 1
Procedure
To a solution of the compound of Formula 104 (8.7 9, 24 mmol) in dichloromethane (250 mL) was added EDC (14.85 g, 77 mmol), and diisopropylethylamine (14.1 mL, 81 mmol). After stirring at room temperature for 1.5 hours, benzylamine (8.4 mL, 77 mmol) was added and the reaction stirred for an additional 48 hours. The mixture was washed with water (2×50 mL), 10% phosphoric acid (2×50 mL), and saturated NaHCO3 (50 mL). The organic phase was dried over MgSO4, filtered and concentrated under vacuum to give a mixture of 9.4 g (88% yield) of the desired product of Formula 105, 2-(2-benzylcarbamoyl-5-chloro-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester, as a light yellow foam, together with a small amount of 2-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-2Hquinzoline-1-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (Formula 106), which was taken on without further purification. LRMS (MH+) m/z 458.
Workup
- stirringthe reaction stirred for an additional 48 hours
- washThe mixture was washed with water (2×50 mL), 10% phosphoric acid (2×50 mL), and saturated NaHCO3 (50 mL)
- dry with materialThe organic phase was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated under vacuum
- customto give
Sources & evidence
- ORD record
- ord-924983f59a61409b9a502dc7aa2b72b5
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07557115B2
Linked notes
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