Diethyl Oxalate → rac-2-(1-Phenoxy-ethyl)-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrazine

HRID 2369606

Reaction equation

HRID 2369606 reaction equation
[O:1]([CH:8]([CH3:12])[C:9](=O)[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C(OCC)=O.C(OC(=O)C(=O)CC(=O)COC1C=CC=CC=1)C.C(OC(C1NN=C(COC2C=CC=CC=2)C=1)=O)C.C(OC([C:64]1[N:65]([CH2:77][CH:78]([NH:80][C:81](OC(C)(C)C)=O)C)[N:66]=C(COC2C=CC=CC=2)C=1)=O)C.CC1CN2N=C(COC3C=CC=CC=3)C=C2C(=O)N1.CC1CN2N=C(COC3C=CC=CC=3)C=C2CN1>>[O:1]([CH:8]([C:9]1[CH:10]=[C:64]2[CH2:81][NH:80][CH2:78][CH2:77][N:65]2[N:66]=1)[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 7

HCID 7268Diethyl OxalateHCID 27644743-Phenoxy-2-butanoneHCID 57435086HCID 57435086, compoundHCID 67958408HCID 67958408, compoundHCID 67960066HCID 67960066, compoundHCID 67960219HCID 67960219, compoundHCID 178469067HCID 178469067, compound

Product 1

HCID 67968152rac-2-(1-Phenoxy-ethyl)-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrazine

Procedure

The compound was prepared from 3-phenoxy-butan-2-one and diethyl oxalate using the methods described in the preceding examples 9 (2,4-dioxo-5-phenoxy-pentanoic acid ethyl ester), 10 (5-phenoxymethyl-2H-pyrazole-3-carboxylic acid ethyl ester), 11 (rac-2-(2-tert-butoxycarbonylamino-propyl)-5-phenoxymethyl-2H-pyrazole-3-carboxylic acid ethyl ester), 12 (rac-6-methyl-2-phenoxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one), and 13 (rac-6-methyl-2-phenoxymethyl-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrazine).

Sources & evidence

ORD record
ord-dc1efb89c4d641b887a2598706db7c49
Source dataset
uspto-grants-2014_04
Patent number
US08703946B2

Linked notes

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