Diisopropylcarbodiimide → Tert-butyl 4-(4-(methylcarbamoyl)phenylcarbamoyl)-3-((pyridin-3-yloxy)methyl)piperazine-1-carboxylate
Reaction equation
[CH:1]([N:4]=C=NC(C)C)(C)C.OC(C(F)(F)F)=O.[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][N:27]([C:30]([NH:32][C:33]2[CH:41]=[CH:40][C:36]([C:37]([OH:39])=O)=[CH:35][CH:34]=2)=[O:31])[CH:26]([CH2:42][O:43][C:44]2[CH:45]=[N:46][CH:47]=[CH:48][CH:49]=2)[CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].Cl.CN.C(N(C(C)C)CC)(C)C.ON1C2C=CC=CC=2N=N1>C(Cl)Cl.CN(C=O)C>[CH3:1][NH:4][C:37]([C:36]1[CH:40]=[CH:41][C:33]([NH:32][C:30]([N:27]2[CH2:28][CH2:29][N:24]([C:22]([O:21][C:17]([CH3:20])([CH3:18])[CH3:19])=[O:23])[CH2:25][CH:26]2[CH2:42][O:43][C:44]2[CH:45]=[N:46][CH:47]=[CH:48][CH:49]=2)=[O:31])=[CH:34][CH:35]=1)=[O:39]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
Diisoproylcarbodiimide (0.037 mL, 0.24 mmol) was added to a solution of 4-(4-(tert-butoxycarbonyl)-2-((pyridin-3-yloxy)methyl)piperazine-1-carboxamido)benzoic acid TFA salt (123 mg, 0.215 mmol), methylamine hydrochloride (16 mg, 0.237 mmol), diisopropylethylamine (0.123 mL, 0.710 mmol), and N-hydroxybenzotriazole (32 mg, 0.237 mmol) in CH2Cl2 (2 mL) and DMF (0.5 mL). After stirring overnight, the reaction mixture was concentrated under reduced pressure and was purified by HPLC (10 to 90% MeCN/0.1% TFA in H2O/0.1% TFA gradient). This gave 103 mg (82%) of the TFA salt of the title compound as a white solid. LC-MS: RT=5.99 min, [M+H]+=470.2.
Workup
- concentrationthe reaction mixture was concentrated under reduced pressure
- customwas purified by HPLC (10 to 90% MeCN/0.1% TFA in H2O/0.1% TFA gradient)
Sources & evidence
- ORD record
- ord-a1be3d116ee74029a5a02200dbbf6a6f
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09428522B2
Reaction notes
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