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

HRID 2374986ノート

反応式

HRID 2374986 の反応式
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

参加物

5

反応物 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-amine2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6fe820f6434f439aaf22282bb9bc1172
出典データセット
uspto-grants-2008_12
特許番号
US07462614B2

反応ノート

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