Diisopropylethylamine → HCID 89442593, compound

HRID 2284014Notes

Reaction equation

HRID 2284014 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1[CH2:9][CH3:10].[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[N:19]=[C:20]([CH:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)[N:21]([CH2:23][CH2:24][N:25]3[CH2:28][CH:27]([F:29])[CH2:26]3)[CH:22]=2)=[CH:14][C:13]=1[C:36]([F:39])([F:38])[F:37].CCN(C(C)C)C(C)C>CS(C)=O>[CH2:9]([C:3]1[C:4]([NH2:8])=[N:5][CH:6]=[N:7][C:2]=1[N:33]1[CH2:32][CH2:31][CH:30]([C:20]2[N:21]([CH2:23][CH2:24][N:25]3[CH2:28][CH:27]([F:29])[CH2:26]3)[CH:22]=[C:18]([C:15]3[CH:16]=[CH:17][C:12]([F:11])=[C:13]([C:36]([F:39])([F:37])[F:38])[CH:14]=3)[N:19]=2)[CH2:35][CH2:34]1)[CH3:10]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 58497086HCID 58497086, compoundHCID 89442750HCID 89442750, compound

Product 1

HCID 89442593HCID 89442593, compoundYield 19.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The reaction mixture of 6-chloro-5-ethyl-pyrimidin-4-ylamine (50.00 mg; 0.32 mmol; 1.00 eq.), 4-(4-(4-fluoro-3-(trifluoromethyl)phenyl)-1-(2-(3-fluoroazetidin-1-yl)ethyl)-1H-imidazol-2-yl)piperidine (138.05 mg; 0.33 mmol; 1.05 eq.) and DIEA (65.77 mg; 0.48 mmol; 1.50 eq.) in DMSO (1.5 ml) was placed in microwave at 125° C. for 1 hr. found small amount desired, mostly was sm, 140° C. for another 1 hr, more product formed, 150° C. for another 1 hr, purified the product by HPLC, collected title compound 33 mg, yield 16%. LC-MS (M+1=536, obsd.=536).

Workup

  1. waitmostly was sm, 140° C. for another 1 hr
  2. custommore product formed, 150° C. for another 1 hr
  3. custompurified the product by HPLC

Sources & evidence

ORD record
ord-6e2e7431a78c431ba98ee93ce7449858
Source dataset
uspto-grants-2015_09
Patent number
US09145392B2

Reaction notes

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