(+/-)(3SR,3aRS)-2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylic acid → HCID 68799668, compound

HRID 505774Notes

Reaction equation

HRID 505774 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[CH:18]([CH:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:17]3[C:12]([C:13]4[CH:27]=[CH:26][C:25]([C:28]([OH:30])=[O:29])=[CH:24][C:14]=4[CH2:15][CH2:16]3)=[N:11]2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]>C(O)CCC>[Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[CH:18]([CH:19]3[CH2:20][CH2:21][CH2:22][CH2:23]3)[CH:17]3[C:12]([C:13]4[CH:27]=[CH:26][C:25]([C:28]([O:30][CH2:3][CH2:2][CH2:7][CH3:6])=[O:29])=[CH:24][C:14]=4[CH2:15][CH2:16]3)=[N:11]2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

3

Reactant 1

HCID 24983760(+/-)(3SR,3aRS)-2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylic acid

Product 1

HCID 68799668HCID 68799668, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

The title compound was prepared from (±)-(3SR,3aRS)-2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylic acid, Example 15 and n-butanol according to Method E. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.94 (t, J=7.38 Hz, 3H), 1.12-1.55 (m, 9H), 1.66-1.75 (m, 3H), 1.83 (ddd, J=25.91, 13.02, 4.03 Hz, 1H), 2.01-2.11 (m, 1H), 2.20-2.27 (m, 1H), 2.85-2.96 (m, 1H), 3.07-3.15 (m, 1H), 3.61 (ddd, J=13.63, 9.33, 4.70 Hz, 1H), 4.29 (t, J=6.44 Hz, 2H), 4.97 (dd, J=9.53, 5.77 Hz, 1H), 7.21 (dd, J=8.86, 1.88 Hz, 1H), 7.42 (d, J=2.15 Hz, 1H), 7.69 (d, J=8.86 Hz, 1H), 7.83 (dd, J=8.32, 1.34 Hz, 1H), 7.87 (s, 1H), 8.12 (d, J=8.32 Hz, 1H); ES-MS m/z 476 (M+H).

Sources & evidence

ORD record
ord-a10697ec77dc46c886317da45002272f
Source dataset
uspto-grants-2010_08
Patent number
US07781428B2

Reaction notes

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