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

HRID 2374970Notes

Reaction equation

HRID 2374970 reaction equation
Br[C:2]1[S:6][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.[Br:45]C1C=CSC=1C(O)=O>>[Br:45][C:4]1[CH:3]=[CH:2][S:6][C:5]=1[C:7]([NH:9][CH:10]([C:12]1[N:17]=[N:16][C:15]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[N:14][CH:13]=1)[CH3:11])=[O:8]

Participants

4

Reactant 3

HCID 27396883-Bromothiophene-2-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 587119833-bromo-N-[1-(3-{[4-(methyloxy)phenyl]amino}1,2,4-triazin-6-yl)ethyl]-2-thiophenecarboxamide

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-bromothiophene-2-carboxylic acid (93 mg, 0.45 mmol), except the reaction was stirred for 6.5 h and purification using silica SPE was omitted, to give 3-bromo-N-[1-(3-{[4-(methyloxy)phenyl]amino}1,2,4-triazin-6-yl)ethyl]-2-thiophenecarboxamide (162 mg) as a yellow solid. MS m/z 434/436 (M+1).

Workup

  1. custompurification

Sources & evidence

ORD record
ord-6ff0d1a8a2f5499ca18ab7be59c7c66b
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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