Water → HCID 178506147, compound

HRID 2283954Notes

Reaction equation

HRID 2283954 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1Cl.[F:9][C:10]([F:29])([F:28])[C:11]1[CH:12]=[C:13]([C:17]2[N:18]=[C:19]([CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[NH:20][CH:21]=2)[CH:14]=[CH:15][CH:16]=1.C(N(CC)C(C)C)(C)C.O>CN1C(=O)CCC1>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[N:25]1[CH2:26][CH2:27][CH:22]([C:19]2[NH:20][CH:21]=[C:17]([C:13]3[CH:14]=[CH:15][CH:16]=[C:11]([C:10]([F:29])([F:28])[F:9])[CH:12]=3)[N:18]=2)[CH2:23][CH2:24]1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 8176963-Bromo-4-chloropyridineHCID 178506150HCID 178506150, compound

Product 1

HCID 178506147HCID 178506147, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 3-bromo-4-chloropyridine (100.0 mg; 0.52 mmol; 1.0 eq.), 4-[4-(3-trifluoromethyl-phenyl)-1h-imidazol-2-yl]-piperidine (153.4 mg; 0.52 mmol; 1.0 eq.), N,N-diisopropylethylamine (0.26 ml; 1.56 mmol; 3.0 eq.) in NMP (2.0 ml) in a microwave vial was heated at 160° C. for 4 h. The reaction mixture was poured into water. The precipitate was filtered, washed with water and dried under vacuum to afford the title compound in 64% yield. LC-MS: (M+1=451, obsd.=451).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-86b7ddc8491244cba41c091374ac0d8e
Source dataset
uspto-grants-2015_09
Patent number
US09145392B2

Reaction notes

Loading…