Thiophene-3-carboxylic acid → N-[1-(3-{[4-(methyloxy)phenyl]amino)-1,2,4-triazin-6-yl)ethyl]-3-thiophenecarboxamide

HRID 2374986노트

반응식

HRID 2374986 반응식
BrC1S[C:5]([C:7]([NH:9][CH:10]([C:12]2[N:17]=[N:16][C:15]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[N:14][CH:13]=2)[CH3:11])=[O:8])=[CH:4][CH:3]=1.NC(C1N=NC(NC2C=CC(OC)=CC=2)=NC=1)C.[S:45]1C=CC(C(O)=O)=[CH:46]1>C(OCC)(=O)C>[CH3:26][O:25][C:22]1[CH:21]=[CH:20][C:19]([NH:18][C:15]2[N:16]=[N:17][C:12]([CH:10]([NH:9][C:7]([C:5]3[CH:4]=[CH:3][S:45][CH:46]=3)=[O:8])[CH3:11])=[CH:13][N:14]=2)=[CH:24][CH:23]=1

참가 물질

5

반응물 3

HCID 6918Thiophene-3-carboxylic acidHCID 587119305-bromo-N-[1-(3-{[4-(methyloxy)phenyl]amino}-1,2,4-triazin-6-yl)ethyl]-2-thiophenecarboxamideHCID 587119996-(1-aminoethyl)-N-[4-(methyloxy)phenyl]-1,2,4-triazin-3-amine2회

생성물 1

HCID 58712012N-[1-(3-{[4-(methyloxy)phenyl]amino)-1,2,4-triazin-6-yl)ethyl]-3-thiophenecarboxamide

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

In a similar manner as described for Intermediate 48, using 6-(1-aminoethyl)-N-[4-(methyloxy)phenyl]-1,2,4-triazin-3-amine (Intermediate 47) (100 mg, 0.41 mmol), and 3-thiophenecarboxylic acid (57 mg, 0.45 mmol). Except, that after 3 hours, the crude reaction mixture was diluted with ethyl acetate and washed twice with dilute aqueous hydrochloric acid (0.2 N) followed by saturated sodium bicarbonate solution. The organic layer was separated, dried with magnesium sulfate, filtered, reduced and then purified by chromatography on silica gel eluting with 40% ethyl acetate, in petrol to afford N-[1-(3-{[4-(methyloxy)phenyl]amino}-1,2,4-triazin-6-yl)ethyl]-3-thiophenecarboxamide (95 mg) as a yellow solid. MS m/z 356 (M+1).

후처리

  1. customthe crude reaction mixture
  2. washwashed twice with dilute aqueous hydrochloric acid (0.2 N)
  3. customThe organic layer was separated
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. custompurified by chromatography on silica gel eluting with 40% ethyl acetate, in petrol

출처 및 근거

ORD 기록
ord-6fe820f6434f439aaf22282bb9bc1172
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07462614B2

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