3,5-Heptanedione → [1-(4-amino-benzyl)-3-cyclopropyl-5-ethyl-1H-pyrazol-4-yl]-acetic acid

HRID 1631907Notes

Reaction equation

HRID 1631907 reaction equation
C([O:3][C:4](=[O:16])[CH2:5][C:6]1[C:7]([CH:13]2[CH2:15][CH2:14]2)=[N:8][NH:9][C:10]=1[CH2:11][CH3:12])C.C(OC(=O)C[C:24]1[C:25]([CH2:31][CH3:32])=N[NH:27][C:28]=1[CH2:29][CH3:30])(C)(C)C.CCC(=O)CC(=O)CC.C(OC(=O)CC1C(C2CCCCC2)=NNC=1C)(C)(C)C>>[NH2:27][C:28]1[CH:24]=[CH:25][C:31]([CH2:32][N:9]2[C:10]([CH2:11][CH3:12])=[C:6]([CH2:5][C:4]([OH:3])=[O:16])[C:7]([CH:13]3[CH2:14][CH2:15]3)=[N:8]2)=[CH:30][CH:29]=1.[NH2:27][C:28]1[CH:24]=[CH:25][C:31]([CH2:32][N:8]2[C:7]([CH:13]3[CH2:14][CH2:15]3)=[C:6]([CH2:5][C:4]([OH:3])=[O:16])[C:10]([CH2:11][CH3:12])=[N:9]2)=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 819233,5-HeptanedioneHCID 66707366(3,5-diethyl-1H-pyrazol-4-yl)-acetic acid tert-butyl esterHCID 66707369(3-cyclohexyl-5-methyl-1H-pyrazol-4-yl)-acetic acid tert-butyl esterHCID 66707499(3-cyclopropyl-5-ethyl-1H-pyrazol-4-yl)-acetic acid ethyl ester

Product 2

HCID 66707371[1-(4-amino-benzyl)-3-cyclopropyl-5-ethyl-1H-pyrazol-4-yl]-acetic acidHCID 66707457[1-(4-amino-benzyl)-5-cyclopropyl-3-ethyl-1H-pyrazol-4-yl]-acetic acid

Procedure

The following examples can be prepared in analogous fashion to example 2.7, employing in the alkylation step (3-cyclopropyl-5-ethyl-1H-pyrazol-4-yl)-acetic acid ethyl ester (preparation according to the preparation of (3,5-diethyl-1H-pyrazol-4-yl)-acetic acid tert-butyl ester, WO2007/141267, employing 2-cyclopropyl-6-ethyl-3,5-dione instead of heptane-3,5-dione) instead of (3-cyclohexyl-5-methyl-1H-pyrazol-4-yl)-acetic acid tert-butyl ester and employing in the amide coupling the corresponding carboxylic acids as coupling partners. Each example is a single regioisomer; the required intermediates [1-(4-amino-benzyl)-3-cyclopropyl-5-ethyl-1H-pyrazol-4-yl]-acetic acid and [1-(4-amino-benzyl)-5-cyclopropyl-3-ethyl-1H-pyrazol-4-yl]-acetic acid are obtained in a single reaction and are separable by MPLC.

Workup

  1. custompreparation

Sources & evidence

ORD record
ord-d2ee93ba3db84074a36d31e3a899fb1b
Source dataset
uspto-grants-2014_07
Patent number
US08791272B2

Reaction notes

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