1,2-Dichloroethane → HCID 86710387, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([OH:16])=O)=[CH:12][N:11]=[CH:10][CH:9]=2)=[C:4]([F:17])[CH:3]=1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.C(Cl)CCl.[F:41][C:42]([F:46])([F:45])[CH2:43][NH2:44]>CN(C=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([NH:44][CH2:43][C:42]([F:46])([F:45])[F:41])=[O:16])=[CH:12][N:11]=[CH:10][CH:9]=2)=[C:4]([F:17])[CH:3]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To stirred solution of 4-(4-chloro-2-fluorophenyl)nicotinic acid (300 mg, 1.192 mmol), prepared as described in Example 2, Part A, in anhydrous DMF (2 mL) under nitrogen was added HOBT (365 mg, 2.384 mmol), DIEA (0.927 mL, 4.77 mmol) and EDC (343 mg, 1.788 mmol). The reaction mixture was cooled to 0° C. and treated with 2,2,2-trifluoroethanamine (236 mg, 2.384 mmol) drop wise and warmed to RT and allowed to stir for 12 h. The reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (2×50 mL). The combined organic layers were dried over sodium sulphate and concentrated under reduced pressure to afford 4-(4-chloro-2-fluorophenyl)-N-(2,2,2-trifluoroethyl)nicotinamide (200 mg, 0.601 mmol, 50% crude yield) as a yellow solid. LC/MS (ESI) m/e 333.2, [(M+H)+, calcd for C14H10ClF4N2O, 333.0]; LC/MS retention time (method A): tR=1.66 min.
Workup
- customprepared
- temperaturewarmed to RT
- extractionextracted with ethyl acetate (2×50 mL)
- dry with materialThe combined organic layers were dried over sodium sulphate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-5814ab1d06fa4668a1f1ea343153472d
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08901305B2
Reaction notes
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