Potassium Carbonate → Ethyl 4-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)quinazoline-2-carboxylate

HRID 2234025Notes

Reaction equation

HRID 2234025 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:3]=1.FC(F)(F)C([O-])=O.[Cl:24][C:25]1[C:29]([Cl:30])=[C:28]([CH3:31])[NH:27][C:26]=1[C:32]([NH:34][CH:35]1[CH2:40][CH2:39][NH2+:38][CH2:37][CH2:36]1)=[O:33].C([O-])([O-])=O.[K+].[K+]>C(O)(C)(C)C>[Cl:24][C:25]1[C:29]([Cl:30])=[C:28]([CH3:31])[NH:27][C:26]=1[C:32]([NH:34][CH:35]1[CH2:40][CH2:39][N:38]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[C:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:3]=2)[CH2:37][CH2:36]1)=[O:33]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 3477840Ethyl 4-chloroquinazoline-2-carboxylateHCID 685798674-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidinium trifluoroacetate2×

Product 1

HCID 68579939Ethyl 4-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)quinazoline-2-carboxylateYield 47.7%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

As described for the synthesis of Example 264, ethyl 4-chloroquinazoline-2-carboxylate (690 mg), 4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidinium trifluoroacetate (Intermediate 86; 1.7 g), and K2CO3 (1.7 g) in 20 ml tert-butanol were combined to yield 662 mg grey solid.

Sources & evidence

ORD record
ord-01f394cbedb1429687c49825429b4852
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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