Trifluoroacetic acid → 3-ethyl-1-(1-methylpyrrolidin-2-yl)-3,4,6,7,8,9-hexahydro-5H-pyrazolo[3,4-c]isoquinolin-5-one

HRID 1034969Notes

Reaction equation

[C:1](O)([C:3](F)(F)F)=[O:2].[N:8]1([C:17](OCC2C=CC=CC=2)=O)[CH2:12][CH2:11][CH2:10][C@@H:9]1[C:13](OC)=O.[CH2:27]([NH:29][NH2:30])[CH3:28].Cl.F[C:33](F)(F)[CH2:34][NH:35]N>>[CH2:27]([N:29]1[C:34]2[NH:35][C:1](=[O:2])[C:3]3[CH2:13][CH2:9][CH2:10][CH2:11][C:12]=3[C:33]=2[C:13]([CH:9]2[CH2:10][CH2:11][CH2:12][N:8]2[CH3:17])=[N:30]1)[CH3:28]

Participants

Reactant 4

HCID 6422Trifluoroacetic acid

HCID 29062Ethylhydrazine

HCID 688167(R)-1-Benzyl 2-methyl pyrrolidine-1,2-dicarboxylate

HCID 21934076(2,2,2-Trifluoroethyl)hydrazinehydrochloride

Product 1

HCID 1363883043-ethyl-1-(1-methylpyrrolidin-2-yl)-3,4,6,7,8,9-hexahydro-5H-pyrazolo[3,4-c]isoquinolin-5-one

Procedure

The title compound was prepared as TFA salt according to procedure for Example 69A-69F, substituting (±)-1-benzyl 2-methyl pyrrolidine-1,2-dicarboxylate for (R)-1-benzyl 2-methyl pyrrolidine-1,2-dicarboxylate and ethylhydrazine for (2,2,2-Trifluoro-ethyl)-hydrazine HCl salt. MS (DCI): m/z 301 (M+H)+; 1H NMR (400 MHz, CD3OD): δ 1.42 (t, J=7.36 Hz, 2H), 1.75-1.91 (m, 4H), 2.02-2.26 (m, 2H), 2.23-2.37 (m, 1H), 2.52 (t, J=5.68 Hz, 2H), 2.59-2.77 (m, 1H), 2.77-2.89 (m, 1H), 2.88-3.03 (m, 1H), 2.96 (s, 3H), 3.26-3.41 (m, 1H), 3.75-3.93 (m, 1H), 4.30 (q, J=7.36 Hz, 2H), 4.96 (t, J=8.29 Hz, 1H).

Sources & evidence

ORD record: ord-e2eef07c5f9e443694a3e7fe253cc877
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546368B2

Reaction notes

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