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

HRID 2374986Notes

Reaction equation

HRID 2374986 reaction equation
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

Participants

5

Reactant 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×

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-6fe820f6434f439aaf22282bb9bc1172
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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