Triethylamine → Methyl 4-(1-(2,5-dichloronicotinamido)cyclopropyl)benzoate
Reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.C(N=C=NCCCN(C)C)C.Cl.[NH2:24][C:25]1([C:28]2[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=2)[CH2:27][CH2:26]1.C(N(CC)CC)C.[NH4+].[Cl-]>CN(C)C=O>[Cl:1][C:2]1[N:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([NH:24][C:25]1([C:28]2[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=2)[CH2:27][CH2:26]1)=[O:6]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2,5-dichloronicotinic acid (1.84 g, 7.06 mmol) in dry dimethylformamide (15 ml) 1-Hydroxybenzotriazole hydrate (1.08 g, 7.06 mmol) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (2.03 g, 10.58 mmol), a solution of methyl 4-(1-aminocyclopropyl)benzoate hydrochloride (D7) (1.67 g, 7.06 mmol) and triethylamine (0.98 ml, 7.06 mmol) in dry dimethylformamide (15 ml) was added and the resulting mixture was stirred 1 h at room temperature. NH4Cl saturated solution (50 ml) was added the mixture was extracted with ethylacetate (3×50 ml). Collected organics, after solvent evaporation, was purified by Biotage column SNAP-Si (50 g) eluting with a mixture dichloromethane/ethylacetate from 100/0 to 95:5. Collected organics after solvent evaporation afforded the title compound (D97) (1.03 mg)
Workup
- extractionwas extracted with ethylacetate (3×50 ml)
- customCollected organics, after solvent evaporation
- customwas purified by Biotage column SNAP-Si (50 g)
- washeluting with a mixture dichloromethane/ethylacetate from 100/0 to 95:5
- customCollected organics after solvent evaporation
Sources & evidence
- ORD record
- ord-6265039ce10947d7bb8f75e2305068aa
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08828987B2
Reaction notes
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