4-[(4-but-2-ynyloxy-benzenesulfonyl)-methyl-amino]-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid

Base Information

• Chemical Name: 4-[(4-but-2-ynyloxy-benzenesulfonyl)-methyl-amino]-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid
• CAS No.: 287379-34-4
• Molecular Formula: C₂₀H₂₀N₄O₅S
• Molecular Weight: 428.469

Synonyms:4-[(4-but-2-ynyloxy-benzenesulfonyl)-methyl-amino]-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid

Chemical Property of 4-[(4-but-2-ynyloxy-benzenesulfonyl)-methyl-amino]-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid

Chemical Property:

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Technology Process of 4-[(4-but-2-ynyloxy-benzenesulfonyl)-methyl-amino]-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid

There total 6 articles about 4-[(4-but-2-ynyloxy-benzenesulfonyl)-methyl-amino]-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

methyl propargyl alcohol (764-01-2) + 4-[(4-fluorobenzenesulfonyl)methylamino]-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid (287379-46-8) → 4-[(4-but-2-ynyloxy-benzenesulfonyl)-methyl-amino]-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid (287379-34-4)

Guidance literature:

methyl propargyl alcohol; 4-[(4-fluorobenzenesulfonyl)methylamino]-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 2h;

Acidic aqueous solution;

Reference yield:

methyl propargyl alcohol (764-01-2) + ethyl 4-[(4-fluorobenzenesulfonyl)methylamino]-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (287379-45-7) → 4-[(4-but-2-ynyloxy-benzenesulfonyl)-methyl-amino]-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid (287379-34-4)

Guidance literature:

methyl propargyl alcohol; With sodium hydride; at 0 ℃; for 0.166667h;

ethyl 4-[(4-fluorobenzenesulfonyl)methylamino]-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate; at 20 ℃; for 3h;

With citric acid; In water;

Reference yield:

5-Amino-1,3-dimethylpyrazole (3524-32-1) → 4-[(4-but-2-ynyloxy-benzenesulfonyl)-methyl-amino]-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid (287379-34-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 120 - 150 °C

1.2: Heating

2.1: POCl₃

3.1: NaH / dimethylformamide

4.1: aq. NaOH

With sodium hydroxide; sodium hydride; trichlorophosphate; In N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(03)00127-6

upstream raw materials:

4-[(4-but-2-ynyloxy-benzenesulfonyl)-methyl-amino]-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester

5-Amino-1,3-dimethylpyrazole

ethyl 4-chloro-1,3-dimethylpyrazolo[3,4-b]pyridine-5-carboxylate

4-hydroxy-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester

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