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 2389852노트

반응식

HRID 2389852 반응식
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

참가 물질

6

반응물 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

생성물 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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8931f93288b74c31a87f4c532b1f34e6
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273752B2

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