Methyl 4-aminobenzoate → 4-(5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-benzoic acid methyl ester

HRID 1784004Notes

Reaction equation

HRID 1784004 reaction equation
CN1CCN(C2C=CC(NC3C4N(N=CN=4)C(C4C=C(C(N)=O)SC=4)=CN=3)=CC=2)CC1.[Br:32][C:33]1[N:38]2[N:39]=[CH:40][N:41]=[C:37]2[C:36](Br)=[N:35][CH:34]=1.[CH3:43][O:44][C:45](=[O:53])[C:46]1[CH:51]=[CH:50][C:49]([NH2:52])=[CH:48][CH:47]=1.C(N(C(C)C)C(C)C)C>CC(O)C>[CH3:43][O:44][C:45](=[O:53])[C:46]1[CH:51]=[CH:50][C:49]([NH:52][C:36]2[C:37]3[N:38]([N:39]=[CH:40][N:41]=3)[C:33]([Br:32])=[CH:34][N:35]=2)=[CH:48][CH:47]=1

Participants

6

Reactant 4

HCID 12082Methyl 4-aminobenzoateHCID 81531DiisopropylethylamineHCID 497580225,8-Dibromo-(1,2,4)triazolo(1,5-a)pyrazineHCID 575899284-{8-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl}-thiophene-2-carboxylic acid amide

Product 1

HCID 575900274-(5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

This compound may be prepared using methods as described for Compound 6, step 1 using 5,8-dibromo-[1,2,4]triazolo[1,5-a]pyrazine (250 mg, 0.90 mmol), 4-aminobenzoic methyl ester (163 mg, 1.08 mmol) and N-ethyldiisopropyl-amine (0.19 mL, 1.08 mmol) in 2-propanol (2.5 mL). The title compound is obtained after trituration with 2-propanol as a brown solid (148 mg, 47%).

Workup

  1. customThis compound may be prepared

Sources & evidence

ORD record
ord-9f5414befd6b43e4b8bf61b0c1b78428
Source dataset
uspto-grants-2009_03
Patent number
US07501411B2

Reaction notes

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