Pyridine → HCID 86674503, compound

HRID 450346Notes

Reaction equation

HRID 450346 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][NH:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:6][CH:5]=[C:4]([Cl:16])[C:3]=1[NH:17][C:18]1[N:39]([CH3:40])[C:21]2=[N:22][C:23]([N:29]3[CH2:34][CH2:33][CH:32]([C:35]([F:38])([F:37])[F:36])[CH2:31][CH2:30]3)=[C:24]([C:26](O)=[O:27])[CH:25]=[C:20]2[N:19]=1.ClC(N(C)C)=C(C)C.[F:49][C:50]([F:60])([F:59])[O:51][C:52]1[CH:58]=[CH:57][C:55]([NH2:56])=[CH:54][CH:53]=1.N1C=CC=CC=1>CC#N.C(Cl)Cl>[F:49][C:50]([F:59])([F:60])[O:51][C:52]1[CH:53]=[CH:54][C:55]([NH:56][C:26]([C:24]2[CH:25]=[C:20]3[N:19]=[C:18]([NH:17][C:3]4[C:4]([Cl:16])=[CH:5][CH:6]=[C:7]([CH2:8][NH:9][C:10](=[O:15])[C:11]([CH3:13])([CH3:14])[CH3:12])[C:2]=4[Cl:1])[N:39]([CH3:40])[C:21]3=[N:22][C:23]=2[N:29]2[CH2:30][CH2:31][CH:32]([C:35]([F:36])([F:38])[F:37])[CH2:33][CH2:34]2)=[O:27])=[CH:57][CH:58]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 6008484-(Trifluoromethoxy)anilineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 67958121HCID 67958121, compound

Product 1

HCID 86674503HCID 86674503, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-{2,6-dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenylamino}-5-[4-trifluoromethyl-piperidinyl]-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid (54 mg, 0.090 mmol), (1-chloro-2-methyl-propenyl)-dimethylamine (0.026 mL, 0.20 mmol) and DCM (2 mL) is stirred for 30 min. This mixture is added to 4-trifluoromethoxyaniline (0.100 mmol) and pyridine (25 μL, 0.32 mmol) in MeCN (1 mL) and it is stirred for 2 h at 40° C. and overnight at 60° C. The mixture is concentrated and the residue is diluted with DMF/water 19/1 (2 mL) and purified via reverse phase HPLC. Yield: 18 mg. HPLC Rt=0.645 min (method G). MS m/z: 760 [M+H]+.

Workup

  1. stirringis stirred for 2 h at 40° C. and overnight at 60° C
  2. concentrationThe mixture is concentrated
  3. additionthe residue is diluted with DMF/water 19/1 (2 mL)
  4. custompurified via reverse phase HPLC

Sources & evidence

ORD record
ord-2183c6d2e4864d92a13806ea8628e635
Source dataset
uspto-grants-2013_07
Patent number
US08486968B2

Reaction notes

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