Reaction equation
[CH:1]1([CH:5]=[C:6]2[CH2:15][CH2:14][C:13]3[CH:12]=[C:11]([C:16]([O:18]C)=[O:17])[CH:10]=[CH:9][C:8]=3[C:7]2=O)[CH2:4][CH2:3][CH2:2]1.Cl.[Cl:22][C:23]1[CH:30]=[C:29]([NH:31][NH2:32])[CH:28]=[CH:27][C:24]=1[C:25]#[N:26]>>[Cl:22][C:23]1[CH:30]=[C:29]([N:31]2[CH:5]([CH:1]3[CH2:4][CH2:3][CH2:2]3)[CH:6]3[C:7]([C:8]4[CH:9]=[CH:10][C:11]([C:16]([OH:18])=[O:17])=[CH:12][C:13]=4[CH2:14][CH2:15]3)=[N:32]2)[CH:28]=[CH:27][C:24]=1[C:25]#[N:26]Participants
Procedure
The title compound was prepared according to Method B and Method C from methyl 6-(cyclobutylmethylene)-5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate; Preparation 19 and 2-chloro-4-hydrazinylbenzonitrile hydrochloride (Preparation 1) to give 2-(3-chloro-4-cyanophenyl)-3-cyclobutyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylic acid (150 mg, 0.36 mmol, 65% yield) as a yellow solid. The title compound was largely present as (±)-(3RS,3aSR)-2-(3-chloro-4-cyanophenyl)-3-cyclobutyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.56-1.77 (m, 4H), 1.77-1.98 (m, 3H), 2.07-2.18 (m, 1H), 2.51-2.59 (m, 1H), 2.80-2.93 (m, 1H), 2.97-3.07 (m, 1H), 3.44-3.56 (m, 1H), 4.88 (dd, J=9.40, 6.98 Hz, 1H), 7.22 (dd, J=8.86, 1.88 Hz, 1H), 7.42 (d, J=2.15 Hz, 1H), 7.67 (d, J=8.86 Hz, 1H), 7.75-7.83 (m, 2H), 8.01 (d, J=8.06 Hz, 1H). ES-MS m/z 420 (M+H)
Workup
- customThe title compound was prepared
Sources & evidence
- ORD record
- ord-b6807ed401514002b947a26d3a30018f
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07781428B2
Linked notes
Loading…