3-Pentanol → (+/-)-(3SR,3aRS)-pentan-3-yl 2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylate

HRID 505763Notes

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].[CH3:31][CH2:32][CH:33](O)[CH2:34][CH3:35]>>[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:33]([CH2:34][CH3:35])[CH2:32][CH3:31])=[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 114283-Pentanol

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 68798445(+/-)-(3SR,3aRS)-pentan-3-yl 2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylate

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 pentan-3-ol according to Method E. 1H NMR (400 MHz, CDCl3) δ ppm 0.97 (t, J=7.38 Hz, 6H), 1.18-1.63 (m, 7H), 1.64-1.81 (m, 4H), 1.96 (ddd, J=26.11, 12.96, 4.16 Hz, 1H), 2.06-2.18 (m, 1H), 2.23-2.40 (m, 1H), 2.83-3.01 (m, 1H), 3.07-3.18 (m, 1H), 3.49 (ddd, J=13.76, 9.33, 4.83 Hz, 1H), 4.64 (dd, J=9.67, 5.37 Hz, 1H), 5.04 (dt, J=12.35, 6.18 Hz, 1H), 7.03 (dd, J=8.86, 2.15 Hz, 1H), 7.30 (d, J=2.15 Hz, 1H), 7.46 (d, J=8.86 Hz, 2H), 7.84-7.99 (m, 2H), 8.15 (d, J=8.06 Hz, 1H).

Sources & evidence

ORD record: ord-09320153e7394bdfa4b2e6bbf04ee31e
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781428B2

Reaction notes

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