Carbonocyanidic acid, methyl ester → HCID 136159789, compound
Reaction equation
[C:1]([C:3]([O:5][CH3:6])=[O:4])#[N:2].[NH2:7][C:8]1[C:12]([C:13]#[N:14])=[C:11]([N:15]2[CH2:20][CH2:19][CH2:18][C@@H:17]([NH:21]C(OC(C)(C)C)=O)[CH2:16]2)[N:10]([CH2:29][C:30]2[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=2[Cl:37])[C:9]=1[C:38](OCC)=[O:39]>Cl.CO>[NH2:21][C@@H:17]1[CH2:18][CH2:19][CH2:20][N:15]([C:11]2[N:10]([CH2:29][C:30]3[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=3[Cl:37])[C:9]3[C:38](=[O:39])[NH:2][C:1]([C:3]([O:5][CH3:6])=[O:4])=[N:7][C:8]=3[C:12]=2[C:13]#[N:14])[CH2:16]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
Methyl cyanoformate (170 μl) was added to a solution of ethyl 3-amino-5-{(3R)-3-[(tertbutoxycarbonyl)amino]piperidin-1-yl}-1-(2-chloro-5-fluorobenzyl)-4-cyano-1H-pyrrole-2-carboxylate (104 mg) in hydrochloric acid-methanol reagent 10 (4 ml), and the resulting mixture was stirred with heating at 90° C. in a sealed tube for 15 hours. The reaction solution was concentrated under reduced pressure and chloroform was added to the residue. The solid precipitated was removed by filtration and the filtrate was concentrated under reduced pressure. To the resulting residue was added diethyl ether, and the solid precipitated was collected by filtration to obtain a crude product of the title compound (107 mg).
Workup
- concentrationThe reaction solution was concentrated under reduced pressure and chloroform
- additionwas added to the residue
- customThe solid precipitated
- customwas removed by filtration
- concentrationthe filtrate was concentrated under reduced pressure
- additionTo the resulting residue was added diethyl ether
- customthe solid precipitated
- filtrationwas collected by filtration
Sources & evidence
- ORD record
- ord-bf7a669b6a694a738e4349584e47a3ec
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07601728B2
Reaction notes
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