Cyclohexanol → HCID 68801729, compound

HRID 505764Notes

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].[CH:31]1(O)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>>[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][CH:31]5[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]5)=[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

Reactant 2

HCID 7966Cyclohexanol

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 68801729HCID 68801729, compound

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 cyclohexanol according to Method E. 1H NMR (400 MHz, CDCl3) δ ppm 1.19-1.68 (m, 13H), 1.70-1.86 (m, 3H), 1.87-2.03 (m, 3H), 2.06-2.20 (m, 1H), 2.23-2.39 (m, 1H), 2.85-2.98 (m, 1H), 3.13 (ddd, J=16.18, 3.36, 3.02 Hz, 1H), 3.49 (ddd, J=13.76, 9.33, 4.83 Hz, 1H), 4.63 (dd, J=9.53, 5.50 Hz, 1H), 5.04 (ddd, J=12.82, 8.93, 3.76 Hz, 1H), 7.02 (dd, J=8.86, 1.88 Hz, 1H), 7.30 (d, J=2.15 Hz, 1H), 7.46 (d, J=8.86 Hz, 1H), 7.87-7.97 (m, 2H), 8.14 (d, J=8.32 Hz, 1H).

Sources & evidence

ORD record: ord-e5f03167540744a6b1f4197187ccc76d
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781428B2

Reaction notes

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