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Hydrochloric Acid → 6-(4-(2-hydroxyethoxy)-3-(trifluoromethyl)phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile

HRID 517993
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HRID 517993 반응식
[NH2:1][C:2]1[C:3]([C:24]#[N:25])=[N:4][C:5]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][OH:19])=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=2)=[CH:6][C:7]=1[NH:8][CH3:9].Cl.[N:27]([O-])=O.[Na+]>O1CCOCC1.O>[OH:19][CH2:18][CH2:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([C:5]2[N:4]=[C:3]([C:24]#[N:25])[C:2]3[N:1]=[N:27][N:8]([CH3:9])[C:7]=3[CH:6]=2)=[CH:11][C:12]=1[C:20]([F:23])([F:21])[F:22]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 709451293-Amino-6-(4-(2-hydroxyethoxy)-3-(trifluoromethyl)phenyl)-4-(methylamino)-picolinonitrile

생성물 1

HCID 672942706-(4-(2-hydroxyethoxy)-3-(trifluoromethyl)phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile수율 51.3%

시약·촉매·용매 2

HCID 962Water
용매
2회
HCID 312751,4-Dioxane용매

실험 절차

3-Amino-6-(4-(2-hydroxyethoxy)-3-(trifluoromethyl)phenyl)-4-(methylamino)-picolinonitrile (11 g) was dissolved in dioxane (20 ml), and water (20 ml). 1M HCl (16.39 ml) was added. Sodium nitrite (2.111 g) in water (2 mL) was added and reaction mixture was stirred at room temperature for 2 hrs. Product crashed out and was filtered, washed with water, ether and dried in oven to give 6-(4-(2-hydroxyethoxy)-3-(trifluoromethyl)phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile (5.7 g) as a pale brown solid. 1H NMR (MeOH) δ: 8.55 (s, 1H), 8.43 (m, 2H), 7.36 (d, 1H), 4.45 (s, 3H), 4.25 (t, 2H), 3.95 (t, 2H). MS m/z 364 (M+H).

후처리

  1. customreaction mixture
  2. filtrationwas filtered
  3. washwashed with water, ether
  4. customdried in oven

출처 및 근거

ORD 기록
ord-801eaf97cadf4df1bc8a397fd519862b
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09115126B2

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