4-Hydroxybenzaldehyde → HCID 178519319, compound

HRID 2360692Notes

Reaction equation

HRID 2360692 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]3[NH:14][N:15]=[C:16]([CH3:17])[C:11]3=[C:10]([C:18]([N:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)=[O:19])[CH:9]=2)=[CH:4][CH:3]=1.[CH:26]1(C2C3C(C(O)=O)=CC(C4C=CC(O)=CC=4)=NC=3NN=2)C[CH2:27]1.C1(C2NN=C(N)C=2)CC1.COC(=O)C(C)=O.OC1C=CC(C=O)=CC=1.N1(C(OC(C)(C)C)=O)CCNCC1>>[CH:17]1([C:16]2[C:11]3[C:12](=[N:13][C:8]([C:5]4[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=4)=[CH:9][C:10]=3[C:18]([N:20]3[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]3)=[O:19])[NH:14][N:15]=2)[CH2:27][CH2:26]1

Participants

7

Reactant 6

HCID 1264-HydroxybenzaldehydeHCID 11748Methyl pyruvateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27580143-cyclopropyl-1H-pyrazol-5-amineHCID 178434395HCID 178434395, compound2×HCID 178524129HCID 178524129, compound

Product 1

HCID 178519319HCID 178519319, compound

Procedure

[3-Cyclopropyl-6-(4-hydroxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-piperazin-1-yl-methanone was prepared following a similar procedure as described for the synthesis of example 53, [6-(4-Hydroxy-phenyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yl]-piperazin-1-yl-methanone, using 3-cyclopropyl-6-(4-hydroxy-phenyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (obtained as described in example 41, steps (a) and (c) employing 5-cyclopropyl-1H-pyrazol-3-ylamine, pyruvic acid methyl ester and 4-hydroxybenzaldehyde as the starting materials) and tert.butyl 1-piperazine carboxylate as starting materials.

Workup

  1. customobtained

Sources & evidence

ORD record
ord-a8e747af503b4964a373dca7f01fbf31
Source dataset
uspto-grants-2014_04
Patent number
US08686150B2

Reaction notes

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