Ethyl Acetate → 6-cyclopropyl-3-methoxy-N-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)pyrazine-2-carboxamide

HRID 588449Notes

Reaction equation

[CH:1]1([C:4]2[N:9]=[C:8]([C:10]([OH:12])=O)[C:7]([O:13][CH3:14])=[N:6][CH:5]=2)[CH2:3][CH2:2]1.[C:15]1([C:21]2[N:30]=[C:24]3[CH:25]=[CH:26][C:27]([NH2:29])=[CH:28][N:23]3[N:22]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CCCP(=O)=O.C(OCC)(=O)C.C(N(CC)C(C)C)(C)C>C(#N)C.O.C1COCC1>[CH:1]1([C:4]2[N:9]=[C:8]([C:10]([NH:29][C:27]3[CH:26]=[CH:25][C:24]4[N:23]([N:22]=[C:21]([C:15]5[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=5)[N:30]=4)[CH:28]=3)=[O:12])[C:7]([O:13][CH3:14])=[N:6][CH:5]=2)[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 70 °C

Procedure

In a 5 ml round bottomed flask 6-cyclopropyl-3-methoxypyrazine-2-carboxylic acid (40 mg, 206 μmol), 2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-6-amine (47.6 mg, 227 μmol) and THF (1 ml) were mixed to form a solution. Then propylphosphonic anhydride in ethyl acetate 50% (328 mg, 301 μl, 515 μmol) and N,N-diisopropylethylamine (106 mg, 144 μl, 824 μmol) were added and the mixture heated to 70° C. for 2 hours. The reaction mixture was allowed to cool to room temperature, then 1.5 ml of acetonitrile:water (1:1) was added and the mixture stirred for 10 minutes. The precipitate formed was then filtered off, washed with 1 ml of acetonitrile:water (1:1) and 1 ml acetonitrile, then dried in vacuo to give 6-cyclopropyl-3-methoxy-N-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)pyrazine-2-carboxamide (45.5 mg, 57.2%) as a yellow solid. MS: m/z=387.2 (M+H+).

Workup

customto form a solution
temperatureto cool to room temperature
customThe precipitate formed
filtrationwas then filtered off
washwashed with 1 ml of acetonitrile:water (1:1) and 1 ml acetonitrile
customdried in vacuo

Sources & evidence

ORD record: ord-c08b2b3b40a84960b3ef4a78655af02c
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09227970B2

Reaction notes

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