Reaction equation
[CH:1]1([CH:6]=[C:7]2[C:16](=O)[C:15]3[C:10](=[CH:11][C:12]([C:18]([O:20]C)=[O:19])=[CH:13][CH:14]=3)[O:9][CH2:8]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[Cl:23][C:24]1[CH:31]=[C:30]([NH:32][NH2:33])[CH:29]=[CH:28][C:25]=1[C:26]#[N:27].O1CCCC1.CN(C)C=O>CO>[Cl:23][C:24]1[CH:31]=[C:30]([N:32]2[CH:6]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[CH:7]3[CH2:8][O:9][C:10]4[CH:11]=[C:12]([C:18]([OH:20])=[O:19])[CH:13]=[CH:14][C:15]=4[C:16]3=[N:33]2)[CH:29]=[CH:28][C:25]=1[C:26]#[N:27]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
The title compound was prepared from methyl 3-(cyclopentylmethylene)-4-oxochroman-7-carboxylate, Preparation 31 (573 mg, 2.0 mmol) and 2-chloro-4-hydrazinylbenzonitrile hydrochloride; Preparation 1 (612 mg, 3.0 mmol) according to Method B and Method C. The crude precipitate was formed from dimethylformamide and methanol to give 2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-2,3,3a,4-tetrahydrochromeno[4,3-c]pyrazole-7-carboxylic acid (yellow solid, 237 mg, 0.563 mmol, 28% yield). The title compound was largely present as (±)-(3RS,3aSR)-2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-2,3,3a,4-tetrahydrochromeno[4,3-c]pyrazole-7-carboxylic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.20 (s, 1H), 7.98 (d, J=8.2 Hz, 1H), 7.70 (d, J=9.0 Hz, 1H), 7.58 (dd, J=8.2, 1.6 Hz, 1H), 7.47 (d, J=1.2 Hz, 1H), 7.41 (d, J=2.0 Hz, 1H), 7.20 (dd, J=8.8, 2.1 Hz, 1H), 4.95 (dd, J=9.4, 7.0 Hz, 1H), 4.78 (dd, J=10.2, 5.9 Hz, 1H), 4.31 (dd, J=13.3, 10.5 Hz, 1H), 4.00 (ddd, J=13.2, 9.7, 5.7 Hz, 1H), 2.03-2.16 (m, 1H), 1.13-1.68 (m, 8H). ES-MS m/z 422 (M+H).
Sources & evidence
- ORD record
- ord-3ac979290a0d4b34ae9747ced31750dc
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07781428B2
Linked notes
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