Dimethyl Sulfoxide → 6-{[2-({2-(Morpholin-4-ylmethyl)-7-[4-(trifluoromethyl)phenyl][1,2,4]triazolo[1,5-c]pyrimidin-5-yl}amino)ethyl]amino}pyridine-3-carbonitrile

HRID 2171585Notes

Reaction equation

HRID 2171585 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([CH2:11][N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[N:10]=[C:6]2[CH:5]=[C:4]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)[N:3]=1.FC(F)(F)C(O)=O.[NH2:35][CH2:36][CH2:37][NH:38][C:39]1[CH:46]=[CH:45][C:42]([C:43]#[N:44])=[CH:41][N:40]=1.CS(C)=O.CCN(C(C)C)C(C)C>C(OCC)(=O)C>[N:12]1([CH2:11][C:9]2[N:10]=[C:6]3[N:7]([C:2]([NH:35][CH2:36][CH2:37][NH:38][C:39]4[N:40]=[CH:41][C:42]([C:43]#[N:44])=[CH:45][CH:46]=4)=[N:3][C:4]([C:18]4[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=4)=[CH:5]3)[N:8]=2)[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 593131385-Chloro-2-(morpholin-4-ylmethyl)-7-[4-(trifluoromethyl)phenyl][1,2,4]triazolo[1,5-c]pyrimidineHCID 687096656-[(2-Aminoethyl)amino]nicotinonitrile trifluoroacetate

Product 1

HCID 687136806-{[2-({2-(Morpholin-4-ylmethyl)-7-[4-(trifluoromethyl)phenyl][1,2,4]triazolo[1,5-c]pyrimidin-5-yl}amino)ethyl]amino}pyridine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

300 mg (0.75 mmol) of 5-chloro-2-(morpholin-4-ylmethyl)-7-[4-(trifluoromethyl)-phenyl][1,2,4]triazolo[1,5-c]pyrimidine (Example 151A) and 180 mg (0.91 mmol) of 6-[(2-aminoethyl)amino]pyridine-3-carbonitrile (Example 13A) are introduced into DMSO (4 ml), 0.79 ml (4.5 mmol) of DIEA is added, and the reaction solution is irradiated in a microwave reactor at 140° C. for 30 min. The reaction mixture is diluted with ethyl acetate, and the organic phase is washed with saturated sodium bicarbonate solution, ammonium chloride solution and saturated sodium chloride solution, dried and concentrated. The residue is taken up in acetonitrile (4 ml), and the solid which precipitates is filtered off and dried. 300 mg (76% of theory) of the product are obtained as a solid.

Workup

  1. additionis added
  2. customthe reaction solution is irradiated in a microwave reactor at 140° C. for 30 min
  3. washthe organic phase is washed with saturated sodium bicarbonate solution, ammonium chloride solution and saturated sodium chloride solution
  4. customdried
  5. concentrationconcentrated
  6. customthe solid which precipitates
  7. filtrationis filtered off
  8. customdried
  9. custom300 mg (76% of theory) of the product are obtained as a solid

Sources & evidence

ORD record
ord-18191093c6ba4905b439f87e0e38f152
Source dataset
uspto-grants-2015_06
Patent number
US09051323B2

Reaction notes

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