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

HRID 1034973Notes

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.[CH:27]([NH:30][NH2:31])([CH3:29])[CH3:28].Cl.F[C:34](F)(F)[CH2:35][NH:36]N>>[CH:27]([N:30]1[C:35]2[NH:36][C:1](=[O:2])[C:3]3[CH2:13][CH2:9][CH2:10][CH2:11][C:12]=3[C:34]=2[C:13]([CH:9]2[CH2:10][CH2:11][CH2:12][N:8]2[CH3:17])=[N:31]1)([CH3:29])[CH3:28]

Participants

Reactant 4

HCID 6422Trifluoroacetic acid

HCID 527891-Isopropylhydrazine

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

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

Product 1

HCID 1363883053-isopropyl-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 isopropylhydrazine for (2,2,2-Trifluoro-ethyl)-hydrazine HCl salt. MS (DCI): m/z 315 (M+H)+; 1H NMR (500 MHz, CD3OD): δ 1.51 (dd, J=6.71, 3.66 Hz, 6H), 1.71-1.95 (m, 3H), 2.05-2.25 (m, 2H), 2.24-2.37 (m, 1H), 2.41-2.56 (m, 2H), 2.69-2.78 (m, 1H), 2.77-2.89 (m, 1H), 2.90-3.03 (m, 1H), 2.96 (s, 3H), 3.29-3.44 (m, 2H), 3.77-3.96 (m, 1H), 4.73-4.91 (m, 2H).

Sources & evidence

ORD record: ord-82c2e2dcef0e455dbd7ca8e19159c51e
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546368B2

Reaction notes

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